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

HRID 979677Notes

Reaction equation

HRID 979677 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 3N--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.

Workup

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

Sources & evidence

ORD record
ord-b56b3c8fdf5d496f9a08a621f738fe45
Source dataset
uspto-grants-1987_05
Patent number
US04668783

Reaction notes

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