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molecular formula C13H10N2O4 B015901 (+)-Thalidomide CAS No. 2614-06-4

(+)-Thalidomide

Cat. No. B015901
M. Wt: 258.23 g/mol
InChI Key: UEJJHQNACJXSKW-UHFFFAOYSA-N
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Patent
US05877200

Procedure details

A stirred mixture of N-phthaloyl-L-glutamine (48.0 g, 174 mmoL), carbonyldiimidazole (30.43 g, 188 mmoL), and 4-dimethylaminopyridine (0.105 g, 0.861 mmoL) in anhydrous tetrahydrofuran (300 mL) is heated to reflux for 16 hours. The reaction slurry is filtered and the solid washed with methylene chloride (200 mL). The solid is air-dried and then dried in vacuo (60° C., <1 mm) to afford 40.40 g (90%) of thalidomide as a white powder. 1HNMR (DMSO-d6) δ 11.16 (s, 1 H, NH), 8.05-7.80 (br s, 4 H, Ar), 5.18 (dd, 1 H, J=12, 5 Hz, CHCO), 3.05-2.85 (m, 1 H, CH2CO), 2,70-2.45 (m, 2 H, CH2CH 2), 2.15-2.00 (M, 1 H, CH2). 13C NMR (DMSO-d6) δ 172.8, 169.8, 167.1, 134.9, 131.2, 123.4, 49.0, 30.9, 22.0.
Quantity
48 g
Type
reactant
Reaction Step One
Quantity
30.43 g
Type
reactant
Reaction Step One
Quantity
0.105 g
Type
catalyst
Reaction Step One
Quantity
300 mL
Type
solvent
Reaction Step One
Yield
90%

Identifiers

REACTION_CXSMILES
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([C@H:12]([C:18]([OH:20])=O)[CH2:13][CH2:14][C:15]([NH2:17])=[O:16])[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C1C=CN=CC=1.O1CCCC1>[CH:2]1[CH:1]=[CH:6][C:5]2[C:7](=[O:8])[N:9]([CH:12]3[C:18](=[O:20])[NH:17][C:15](=[O:16])[CH2:14][CH2:13]3)[C:10](=[O:11])[C:4]=2[CH:3]=1

Inputs

Step One
Name
Quantity
48 g
Type
reactant
Smiles
C1=CC=C2C(=C1)C(=O)N(C2=O)[C@@H](CCC(=O)N)C(=O)O
Name
Quantity
30.43 g
Type
reactant
Smiles
C(=O)(N1C=NC=C1)N1C=NC=C1
Name
Quantity
0.105 g
Type
catalyst
Smiles
CN(C1=CC=NC=C1)C
Name
Quantity
300 mL
Type
solvent
Smiles
O1CCCC1

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
is heated
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for 16 hours
Duration
16 h
FILTRATION
Type
FILTRATION
Details
The reaction slurry is filtered
WASH
Type
WASH
Details
the solid washed with methylene chloride (200 mL)
CUSTOM
Type
CUSTOM
Details
The solid is air-dried
CUSTOM
Type
CUSTOM
Details
dried in vacuo (60° C., <1 mm)

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)C(=O)N(C2=O)C3CCC(=O)NC3=O
Measurements
Type Value Analysis
AMOUNT: MASS 40.4 g
YIELD: PERCENTYIELD 90%
YIELD: CALCULATEDPERCENTYIELD 90%

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
US05877200

Procedure details

A stirred mixture of N-phthaloyl-L-glutamine (48.0 g, 174 mmoL), carbonyldiimidazole (30.43 g, 188 mmoL), and 4-dimethylaminopyridine (0.105 g, 0.861 mmoL) in anhydrous tetrahydrofuran (300 mL) is heated to reflux for 16 hours. The reaction slurry is filtered and the solid washed with methylene chloride (200 mL). The solid is air-dried and then dried in vacuo (60° C., <1 mm) to afford 40.40 g (90%) of thalidomide as a white powder. 1HNMR (DMSO-d6) δ 11.16 (s, 1 H, NH), 8.05-7.80 (br s, 4 H, Ar), 5.18 (dd, 1 H, J=12, 5 Hz, CHCO), 3.05-2.85 (m, 1 H, CH2CO), 2,70-2.45 (m, 2 H, CH2CH 2), 2.15-2.00 (M, 1 H, CH2). 13C NMR (DMSO-d6) δ 172.8, 169.8, 167.1, 134.9, 131.2, 123.4, 49.0, 30.9, 22.0.
Quantity
48 g
Type
reactant
Reaction Step One
Quantity
30.43 g
Type
reactant
Reaction Step One
Quantity
0.105 g
Type
catalyst
Reaction Step One
Quantity
300 mL
Type
solvent
Reaction Step One
Yield
90%

Identifiers

REACTION_CXSMILES
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([C@H:12]([C:18]([OH:20])=O)[CH2:13][CH2:14][C:15]([NH2:17])=[O:16])[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C1C=CN=CC=1.O1CCCC1>[CH:2]1[CH:1]=[CH:6][C:5]2[C:7](=[O:8])[N:9]([CH:12]3[C:18](=[O:20])[NH:17][C:15](=[O:16])[CH2:14][CH2:13]3)[C:10](=[O:11])[C:4]=2[CH:3]=1

Inputs

Step One
Name
Quantity
48 g
Type
reactant
Smiles
C1=CC=C2C(=C1)C(=O)N(C2=O)[C@@H](CCC(=O)N)C(=O)O
Name
Quantity
30.43 g
Type
reactant
Smiles
C(=O)(N1C=NC=C1)N1C=NC=C1
Name
Quantity
0.105 g
Type
catalyst
Smiles
CN(C1=CC=NC=C1)C
Name
Quantity
300 mL
Type
solvent
Smiles
O1CCCC1

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
is heated
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for 16 hours
Duration
16 h
FILTRATION
Type
FILTRATION
Details
The reaction slurry is filtered
WASH
Type
WASH
Details
the solid washed with methylene chloride (200 mL)
CUSTOM
Type
CUSTOM
Details
The solid is air-dried
CUSTOM
Type
CUSTOM
Details
dried in vacuo (60° C., <1 mm)

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)C(=O)N(C2=O)C3CCC(=O)NC3=O
Measurements
Type Value Analysis
AMOUNT: MASS 40.4 g
YIELD: PERCENTYIELD 90%
YIELD: CALCULATEDPERCENTYIELD 90%

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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