Ethyl Acetate → HCID 20157447, compound

HRID 986392Notes

Reaction equation

HRID 986392 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[N:13]2[C:9]([S:10][CH:11]=[CH:12]2)=[N:8][C:7]=1[CH3:14])=[O:5].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O.C(Cl)(Cl)Cl>[CH2:19]([O:18][C:16]([NH:2][CH2:3][C:4]([C:6]1[N:13]2[C:9]([S:10][CH:11]=[CH:12]2)=[N:8][C:7]=1[CH3:14])=[O:5])=[O:17])[CH3:20]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 20157433HCID 20157433, compound

Product 1

HCID 20157447HCID 20157447, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of 4 g of 5-aminoacetyl-6-methylimidazo[2,1-b]thiazole hydrochloride in 50 ml of water is added a mixed solution of 3.2 g of ethyl chloroformate and 50 ml of ethyl acetate under stirring, and then 7.6 g of sodium bicarbonate is added. After the mixture is stirred at room temperature for 4 hours, chloroform and water are added to the resulting mixture. The chloroform layer is separated, washed with water and dried over magnesium sulfate, and then the chloroform is distilled off under reduced pressure. The residual oil is purified with a column chromatography using chloroform as a eluent to give 2 g of 5-ethoxycarbonylaminoacetyl-6-methylimidazo[2,1-b]thiazole.

Workup

  1. stirringAfter the mixture is stirred at room temperature for 4 hours
  2. customThe chloroform layer is separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe chloroform is distilled off under reduced pressure
  6. customThe residual oil is purified with a column chromatography

Sources & evidence

ORD record
ord-e47976cde2d34329b393c94b25b1aa7e
Source dataset
uspto-grants-1987_12
Patent number
US04713381

Reaction notes

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