Phenyl isocyanate → Ethyl 2-(3-phenylureido)thiazol-4-ylglyoxylate

HRID 2107222Notes

Reaction equation

HRID 2107222 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[C:14]1([NH:20][C:21](=[O:22])[NH:1][C:2]2[S:3][CH:4]=[C:5]([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

Product 1

HCID 15053489Ethyl 2-(3-phenylureido)thiazol-4-ylglyoxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g of ethyl 2-aminothiazol-4-ylglyoxylate were dissolved in 100 ml of dimethylformamide, and 7.14 g of phenyl isocyanate were added dropwise to the resulting solution under ice-cooling. The mixture was left to stand overnight, and the dimethylformamide was then evaporated off under reduced pressure. The crystals thus obtained were washed with water, dried and recrystallized from ethyl acetate, giving the desired compound as yellow crystals.

Workup

  1. temperaturecooling
  2. waitThe mixture was left
  3. customthe dimethylformamide was then evaporated off under reduced pressure
  4. customThe crystals thus obtained
  5. washwere washed with water
  6. customdried
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0cbc080d032b423499340506011ccb3b
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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