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molecular formula C10H13ClN2O3S B586757 Chlorpropamide-d4 CAS No. 1794779-79-5

Chlorpropamide-d4

Cat. No. B586757
M. Wt: 280.759
InChI Key: RKWGIWYCVPQPMF-LNFUJOGGSA-N
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Patent
US04062889

Procedure details

n-Propylamine (5.9 g., 0.1 mole.) and propylene carbonate (10.2 g., 0.1 mole.) were mixed and heated at 60° over night. To the resulting hydroxypropyl-n-propylcarbomate were added p-chlorobenzene sulfonamide (10.67 g., as sodium salt) and DMF (200 ml.) and the mixture was heated at 120° for 4 hours. After evaporation of the solvent the residue was taken up in water (200 ml.) and the solution adjusted to pH 8 by the addition of acetic acid. Unreacted p-chlorobenzene sulfonamide (2 g.) separated out and was collected. Further adjustment to pH 5 precipitated 1-(4-chloro-benzenesulfonyl)-3-n-propyl-urea (2 g.) whose infrared spectrum was identical with that of an authentic sample.
Quantity
5.9 g
Type
reactant
Reaction Step One
Quantity
10.2 g
Type
reactant
Reaction Step One
[Compound]
Name
hydroxypropyl-n-propylcarbomate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
10.67 g
Type
reactant
Reaction Step Two
Name
Quantity
200 mL
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH2:1]([NH2:4])[CH2:2][CH3:3].[C:5]1(=O)OC(C)C[O:6]1.[CH:12]1[C:17]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:16][CH:15]=[C:14]([Cl:22])[CH:13]=1>CN(C=O)C>[Cl:22][C:14]1[CH:13]=[CH:12][C:17]([S:18]([NH:21][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])(=[O:20])=[O:19])=[CH:16][CH:15]=1

Inputs

Step One
Name
Quantity
5.9 g
Type
reactant
Smiles
C(CC)N
Name
Quantity
10.2 g
Type
reactant
Smiles
C1(OCC(C)O1)=O
Step Two
Name
hydroxypropyl-n-propylcarbomate
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
10.67 g
Type
reactant
Smiles
C1=CC(=CC=C1S(=O)(=O)N)Cl
Name
Quantity
200 mL
Type
solvent
Smiles
CN(C)C=O

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
heated at 60° over night
TEMPERATURE
Type
TEMPERATURE
Details
the mixture was heated at 120° for 4 hours
Duration
4 h
CUSTOM
Type
CUSTOM
Details
After evaporation of the solvent the residue
ADDITION
Type
ADDITION
Details
the solution adjusted to pH 8 by the addition of acetic acid
CUSTOM
Type
CUSTOM
Details
Unreacted p-chlorobenzene sulfonamide (2 g.) separated out
CUSTOM
Type
CUSTOM
Details
was collected
CUSTOM
Type
CUSTOM
Details
Further adjustment to pH 5 precipitated 1-(4-chloro-benzenesulfonyl)-3-n-propyl-urea (2 g.) whose

Outcomes

Product
Name
Type
Smiles
ClC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCC

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
US04062889

Procedure details

n-Propylamine (5.9 g., 0.1 mole.) and propylene carbonate (10.2 g., 0.1 mole.) were mixed and heated at 60° over night. To the resulting hydroxypropyl-n-propylcarbomate were added p-chlorobenzene sulfonamide (10.67 g., as sodium salt) and DMF (200 ml.) and the mixture was heated at 120° for 4 hours. After evaporation of the solvent the residue was taken up in water (200 ml.) and the solution adjusted to pH 8 by the addition of acetic acid. Unreacted p-chlorobenzene sulfonamide (2 g.) separated out and was collected. Further adjustment to pH 5 precipitated 1-(4-chloro-benzenesulfonyl)-3-n-propyl-urea (2 g.) whose infrared spectrum was identical with that of an authentic sample.
Quantity
5.9 g
Type
reactant
Reaction Step One
Quantity
10.2 g
Type
reactant
Reaction Step One
[Compound]
Name
hydroxypropyl-n-propylcarbomate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
10.67 g
Type
reactant
Reaction Step Two
Name
Quantity
200 mL
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH2:1]([NH2:4])[CH2:2][CH3:3].[C:5]1(=O)OC(C)C[O:6]1.[CH:12]1[C:17]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:16][CH:15]=[C:14]([Cl:22])[CH:13]=1>CN(C=O)C>[Cl:22][C:14]1[CH:13]=[CH:12][C:17]([S:18]([NH:21][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])(=[O:20])=[O:19])=[CH:16][CH:15]=1

Inputs

Step One
Name
Quantity
5.9 g
Type
reactant
Smiles
C(CC)N
Name
Quantity
10.2 g
Type
reactant
Smiles
C1(OCC(C)O1)=O
Step Two
Name
hydroxypropyl-n-propylcarbomate
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
Quantity
10.67 g
Type
reactant
Smiles
C1=CC(=CC=C1S(=O)(=O)N)Cl
Name
Quantity
200 mL
Type
solvent
Smiles
CN(C)C=O

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
heated at 60° over night
TEMPERATURE
Type
TEMPERATURE
Details
the mixture was heated at 120° for 4 hours
Duration
4 h
CUSTOM
Type
CUSTOM
Details
After evaporation of the solvent the residue
ADDITION
Type
ADDITION
Details
the solution adjusted to pH 8 by the addition of acetic acid
CUSTOM
Type
CUSTOM
Details
Unreacted p-chlorobenzene sulfonamide (2 g.) separated out
CUSTOM
Type
CUSTOM
Details
was collected
CUSTOM
Type
CUSTOM
Details
Further adjustment to pH 5 precipitated 1-(4-chloro-benzenesulfonyl)-3-n-propyl-urea (2 g.) whose

Outcomes

Product
Name
Type
Smiles
ClC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCC

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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