N,N-Dimethylaniline → Ethyl alpha-methoxyimino-[2-(beta,beta,beta-trichloroethoxycarbonylamino)thiazol-4-yl)acetate

HRID 223617Notes

Reaction equation

HRID 223617 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10](=O)[CH2:11]Br)[C:5]([O:7][CH2:8][CH3:9])=[O:6].CN(C)C1C=CC=CC=1.[Cl:23][C:24]([Cl:34])([Cl:33])[CH2:25][O:26][C:27]([NH:29][C:30]([NH2:32])=[S:31])=[O:28]>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:32]=[C:30]([NH:29][C:27]([O:26][CH2:25][C:24]([Cl:33])([Cl:23])[Cl:34])=[O:28])[S:31][CH:11]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 130920372,2,2-Trichloroethyl carbamothioylcarbamateHCID 54053279Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-, ethyl ester

Product 1

HCID 54457368Ethyl alpha-methoxyimino-[2-(beta,beta,beta-trichloroethoxycarbonylamino)thiazol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.2 g. of ethyl α-methoxyimino-β-oxo-γ-bromobutyrate in 40 ml. of ethanol are added 1.22 g. of dimethylaniline and 2.2 g. of N-(β,β,β-trichloroethoxycarbonyl)thiourea. The mixture is heated for 1.5 hours under reflux and concentrated under reduced pressure. The concentrate of the reaction mixture is recrystallized from ligroin to give ethyl α-methoxyimino-[2-(β,β,β-trichloroethoxycarbonylamino)thiazol-4-yl]acetate as crystals. 1.84 g. Melting point: 125°-128° C.

Workup

  1. temperatureThe mixture is heated for 1.5 hours
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. concentrationThe concentrate of the reaction mixture
  5. customis recrystallized from ligroin

Sources & evidence

ORD record
ord-3f76498cb980435e8d1d123a6e87df39
Source dataset
uspto-grants-1982_10
Patent number
US04355160

Reaction notes

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