N,N-Dimethylaniline → Ethyl alpha-acetamido-2-(beta,beta,beta-trichloroethoxycarbonylamino)thiazol-4-ylacetate

HRID 1395832Notes

Reaction equation

HRID 1395832 reaction equation
[Cl:1][C:2]([Cl:12])([Cl:11])[CH2:3][O:4][C:5]([NH:7][C:8]([NH2:10])=[S:9])=[O:6].[C:13]([NH:16][CH:17]([C:23](=O)[CH2:24]Br)[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:15])[CH3:14].CN(C)C1C=CC=CC=1>C(O)C>[C:13]([NH:16][CH:17]([C:23]1[N:10]=[C:8]([NH:7][C:5]([O:4][CH2:3][C:2]([Cl:1])([Cl:11])[Cl:12])=[O:6])[S:9][CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 130920372,2,2-Trichloroethyl carbamothioylcarbamateHCID 15137540Ethyl 2-acetamido-4-bromo-3-oxobutanoate

Product 1

HCID 12763197Ethyl alpha-acetamido-2-(beta,beta,beta-trichloroethoxycarbonylamino)thiazol-4-ylacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.51 g. of N-(β,β,β-trichloroethoxycarbonyl)thiourea and 2.66 g. of ethyl α-acetamido-β-oxo-γ-bromobutyrate in 50 ml. of ethanol is added 1.8 g. of N,N-dimethylaniline. The mixture is stirred for 24 hours at room temperature, and condensed under reduced pressure. The residue is dissolved in 30 ml. chloroform and the solution is washed with 3 N-HCl, water, and dried. The solid matter which is obtained by removal of chloroform is purified by silica gel chromatography to give ethyl α-acetamido-2-(β,β,β-trichloroethoxycarbonylamino)thiazol-4-ylacetate. 1.43 g. Melting point: 161.9° C.

Workup

  1. customcondensed under reduced pressure
  2. dissolutionThe residue is dissolved in 30 ml
  3. washchloroform and the solution is washed with 3 N-HCl, water
  4. customdried
  5. customThe solid matter which is obtained by removal of chloroform
  6. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-b6a9d0f518364cc7b2b7ad5844342c94
Source dataset
uspto-grants-1980_05
Patent number
US04205180

Reaction notes

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