Ethanol → HCID 13079788, compound

HRID 1284089Notes

Reaction equation

HRID 1284089 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.C(O)C.[NH2:20][C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1>C1C=CC=CC=1>[N:20]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=2)=[CH:2][N:22]2[CH:23]=[CH:24][CH:25]=[N:26][C:21]=12

Participants

5

Reactant 3

HCID 702EthanolHCID 79782-AminopyrimidineHCID 12399236HCID 12399236, compound

Product 1

HCID 13079788HCID 13079788, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 48 g of ethyl 4-(chloroacetyl)phenylacetate, 100 ml of ethanol and 38 g of 2-aminopyrimidine is heated under reflux for 3 hours. The ethanol is distilled off under reduced pressure, and water is added to the residue. The mixture is extracted with ethyl acetate, and the extract is washed with water, dried and concentrated to give a brown oil. To the oil is added benzene, and the crystalline precipitate is filtered off and recrystallized from ethyl acetate to give 26 g of ethyl 4-(imidazo[1,2-a]-pyrimidine-2-yl)phenylacetate as pale brown crystals melting at 155°-158°C.

Workup

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

Sources & evidence

ORD record
ord-e190c8ea8dea477bb72a0551ba2b2060
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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