N,N-Dimethylaniline → 2-(beta,beta,beta-Trichloroethoxycarbonyl)amino-4-formylthiazole

HRID 1080859Notes

Reaction equation

HRID 1080859 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].BrC(Br)C(CBr)=[O:16].CN(C)[C:22]1[CH:27]=CC=C[CH:23]=1>C(O)C>[Cl:12][C:2]([Cl:1])([Cl:11])[CH2:3][O:4][C:5]([NH:7][C:8]1[S:9][CH:23]=[C:22]([CH:27]=[O:16])[N:10]=1)=[O:6]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 3146661,1,3-Tribromo-2-propanoneHCID 130920372,2,2-Trichloroethyl carbamothioylcarbamate

Product 1

HCID 127632072-(beta,beta,beta-Trichloroethoxycarbonyl)amino-4-formylthiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.0 g. of N-(β,β,β-trichloroethoxycarbonyl)thiourea, 12.0 g. of 1,1,3-tribromoacetone and 5.0 g. of dimethylaniline in 100 ml. of ethanol is heated under reflux for 2 hours. After cooling, ethanol is removed under reduced pressure, and the oily residue is dissolved in ethyl acetate. Ethyl acetate layer is washed with water and dried over MgSO4. Ethyl acetate is removed under reduced pressure and the oily residue is dissolved in small quantity of chloroform. From the solution which is allowed to stand at room temperature is obtained 2-(β,β,β-trichloroethoxycarbonyl)amino-4-formylthiazole as a crystalline form. 5.0 g. Melting point: 188°-190° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. customethanol is removed under reduced pressure
  4. dissolutionthe oily residue is dissolved in ethyl acetate
  5. washEthyl acetate layer is washed with water
  6. dry with materialdried over MgSO4
  7. customEthyl acetate is removed under reduced pressure
  8. dissolutionthe oily residue is dissolved in small quantity of chloroform
  9. customto stand at room temperature

Sources & evidence

ORD record
ord-837399dc0f104f7ebfcbebf7804fb4f7
Source dataset
uspto-grants-1996_12
Patent number
US05583216

Reaction notes

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