2-Aminothiazole → HCID 13079789, compound

HRID 1284091Notes

Reaction equation

HRID 1284091 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)=O.[NH2:17][C:18]1[S:19][CH:20]=[CH:21][N:22]=1>C(O)C>[S:19]1[CH:20]=[CH:21][N:22]2[CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=3)[N:17]=[C:18]12

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 12399236HCID 12399236, compound

Product 1

HCID 13079789HCID 13079789, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 38 g of ethyl 4-(chloroacetyl)phenylacetate, 60 ml of ethanol and 32 g of 2-aminothiazole is heated under reflux for 2 hours. The ethanol is distilled off under reduced pressure, and water is added to the residue. The mixture is extracted with benzene, and the extract is washed with water, dried and concentrated. To the residual reddish brown oil are added benzene and isopropyl ether, and the crystalline precipitate is filtered off and recrystallized from ethanol to give 14 g of ethyl 4-(imidazo[2,1-b]-thiazol-6-yl)phenylacetate as colorless crystals melting at 117°-119°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. distillationThe ethanol is distilled off under reduced pressure, and water
  4. additionis added to the residue
  5. extractionThe mixture is extracted with benzene
  6. washthe extract is washed with water
  7. customdried
  8. concentrationconcentrated
  9. additionTo the residual reddish brown oil are added benzene and isopropyl ether
  10. filtrationthe crystalline precipitate is filtered off
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e7e8f4f7c2bd44029754b4a61633afbf
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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