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molecular formula Cl2 B1223078 Chlorine CAS No. 7782-50-5

Chlorine

Cat. No. B1223078
M. Wt: 70.90 g/mol
InChI Key: KZBUYRJDOAKODT-UHFFFAOYSA-N
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Patent
US04223133

Procedure details

A solution of triphenyl phosphite-chloride kinetic complex was prepared by adding chlorine and triphenyl phosphite (36.8 ml., 3.5 equivalents per equivalent of cephem sulfoxide used below -22.3 g.) simultaneously to 150 ml. of methylene chloride at about -20° to about -10° C., maintaining a pale yellow color in the reaction mixture throughout the co-addition. With the addition of the last drops of triphenyl phosphite to the mixture, it gave a negative starch-iodide test for chlorine. After cooling the mixture to -25° C., 5.1 ml. of amylene and subsequently 22.3 gm. of 4'-nitrobenzyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate, 1-oxide were added. After stirring 25 minutes at -15° to -10° C., the dropwise addition of 11 ml. (3.4 equivalents per equivalent of cephem sulfoxide) of pyridine in 30 ml. of methylene chloride was begun. Pyridine addition was extended over 53 minutes. Fifteen minutes after pyridine addition was complete, 37 ml. (10 equivalents) of isobutanol was added and HCl was bubbled into the reaction mixture for 6 minutes. The title product crystallized from solution and was isolated by filtration, washed with 100 ml. of methylene chloride and dried in vacuo. Yield--6.4 g. (37%).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
36.8 mL
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
[Cl:1][Cl:2].[P:3]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl>[Cl-:1].[P:3]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[Cl:1][Cl:2] |f:3.4|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClCl
Name
Quantity
36.8 mL
Type
reactant
Smiles
P(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
P(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1
Step Three
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(Cl)Cl

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Outcomes

Product
Name
Type
product
Smiles
[Cl-].P(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1
Name
Type
product
Smiles
Name
Type
product
Smiles
ClCl

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04223133

Procedure details

A solution of triphenyl phosphite-chloride kinetic complex was prepared by adding chlorine and triphenyl phosphite (36.8 ml., 3.5 equivalents per equivalent of cephem sulfoxide used below -22.3 g.) simultaneously to 150 ml. of methylene chloride at about -20° to about -10° C., maintaining a pale yellow color in the reaction mixture throughout the co-addition. With the addition of the last drops of triphenyl phosphite to the mixture, it gave a negative starch-iodide test for chlorine. After cooling the mixture to -25° C., 5.1 ml. of amylene and subsequently 22.3 gm. of 4'-nitrobenzyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate, 1-oxide were added. After stirring 25 minutes at -15° to -10° C., the dropwise addition of 11 ml. (3.4 equivalents per equivalent of cephem sulfoxide) of pyridine in 30 ml. of methylene chloride was begun. Pyridine addition was extended over 53 minutes. Fifteen minutes after pyridine addition was complete, 37 ml. (10 equivalents) of isobutanol was added and HCl was bubbled into the reaction mixture for 6 minutes. The title product crystallized from solution and was isolated by filtration, washed with 100 ml. of methylene chloride and dried in vacuo. Yield--6.4 g. (37%).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
36.8 mL
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
[Cl:1][Cl:2].[P:3]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl>[Cl-:1].[P:3]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[Cl:1][Cl:2] |f:3.4|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClCl
Name
Quantity
36.8 mL
Type
reactant
Smiles
P(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
P(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1
Step Three
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(Cl)Cl

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Outcomes

Product
Name
Type
product
Smiles
[Cl-].P(OC1=CC=CC=C1)(OC1=CC=CC=C1)OC1=CC=CC=C1
Name
Type
product
Smiles
Name
Type
product
Smiles
ClCl

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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