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

HRID 979675Notes

Reaction equation

HRID 979675 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-918a4098264c4fb89620edc688c6f965
Source dataset
uspto-grants-1987_05
Patent number
US04668783

Reaction notes

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