Water → alpha-Methoxyimino-[2-(beta,beta,beta-trichloroethoxycarbonylamino)thiazol-4-yl]acetic acid

HRID 979676Notes

Reaction equation

HRID 979676 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:11]=[C:12]([NH:15][C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17])[S:13][CH:14]=1)[C:5]([O:7]CC)=[O:6].[OH-].[K+].O>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:11]=[C:12]([NH:15][C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:21])[Cl:22])=[O:17])[S:13][CH:14]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 54457368Ethyl alpha-methoxyimino-[2-(beta,beta,beta-trichloroethoxycarbonylamino)thiazol-4-yl)acetate

Product 1

HCID 53717109alpha-Methoxyimino-[2-(beta,beta,beta-trichloroethoxycarbonylamino)thiazol-4-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 8.1 g. of ethyl α-methoxyimino-[2-(β,β,β-trichloroethoxycarbonylamino)thiazol-4-yl]acetate in 50 ml. of ethanol is added a solution of 11.2 g. of KOH in a mixture of 30 ml. of water and 150 ml. of ethanol. The whole mixture is stirred at room temperature for 1 hour, and then concentrated under reduced pressure. The residue is extracted with ethyl acetate. The water layer is made acidic with 10% aq. HCl and the separated solid is collected. Recrystallization of the solid from aq. methanol gives α-methoxyimino-[2-(β,β,β-trichloroethoxycarbonylamino)thiazol-4-yl]acetic acid. 4.1 g.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe residue is extracted with ethyl acetate
  3. customthe separated solid is collected
  4. customRecrystallization of the solid from aq. methanol

Sources & evidence

ORD record
ord-fa79c193261a4db0904811306b89cf5f
Source dataset
uspto-grants-1987_05
Patent number
US04668783

Reaction notes

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