Acetic Anhydride → HCID 15725088, compound

HRID 867423Notes

Reaction equation

HRID 867423 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[NH:19][C@@H:18]([C:20]([OH:22])=[O:21])[C:17]([CH3:24])([CH3:23])[S:16]2)=[CH:11][CH:10]=1>O>[C:1]([N:19]1[C@@H:18]([C:20]([OH:22])=[O:21])[C:17]([CH3:24])([CH3:23])[S:16][C@H:15]1[C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2825598(4S)-2-(4-Chlorophenyl)-5,5-dimethyl-4-thiazolidinecarboxylic acid

Product 1

HCID 15725088HCID 15725088, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.6 ml of acetic anhydride are given to a suspension containing 2.71 g (10 mmoles) of 2-(4-chlorophenyl)-5,5-dimethylthiazolidine-4(S)-carboxylic acid in 5.6 ml of hot water and the mixture is kept at 100° C. for 8 minutes. A complete solution is obtained. On cooling, the product precipitates to give the title compound in a yield of 2.39 g (76.1%) which is recrystallized from ethanol by adding water, m.p.: 203°-205° C., [α]D22 =+111.5° (c=1.44, dimethylsulphoxide).

Workup

  1. customA complete solution is obtained
  2. temperatureOn cooling
  3. customthe product precipitates

Sources & evidence

ORD record
ord-de03737a281c42dd882d5acde6f2f4c8
Source dataset
uspto-grants-1988_10
Patent number
US04775675

Reaction notes

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