Acetic Acid → HCID 20391101, compound

HRID 426506Notes

Reaction equation

HRID 426506 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C@H:9]([C:22](O)=[O:23])[C:10]([S:13][C:14](=[S:21])[NH:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])([CH3:12])[CH3:11])=[O:7])=[CH:4][CH:3]=1.C(O)(=O)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH:9]2[C:10]([CH3:12])([CH3:11])[S:13][C:14](=[S:21])[N:15]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:22]2=[O:23])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 22808649HCID 22808649, compound

Product 1

HCID 20391101HCID 20391101, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 10 g of N-(p-chlorobenzoyl)-S-(2-dimethylaminoethylthiocarbamoyl)-penicillamine, 2 g of glacial acetic acid and 100 ml of chloroform is stirred under reflux for 5 hours. The solvent is then removed under reduced pressure, and the crude product is recrystallized from a mixture of ethyl acetate and isopropyl ether to give 5-(p-chlorobenzamido)-3-(2-dimethylaminoethyl)-6,6-dimethyl-2-thioxo-tetrahydro-2H-1,3-thiazin-4-one as pale yellow crystals, melting at 152°-153° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe solvent is then removed under reduced pressure
  3. customthe crude product is recrystallized from a mixture of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-5c725a9d72674e9898e6026f3052ada7
Source dataset
uspto-grants-1979_10
Patent number
US04169899

Reaction notes

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