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

HRID 1074244Notes

Reaction equation

HRID 1074244 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.

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-13f57d86975c43a888b2e1c843035f94
Source dataset
uspto-grants-1990_11
Patent number
US04973684

Reaction notes

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