Ethyl 2-chloroacetoacetate → HCID 70027810, compound

HRID 478844Notes

Reaction equation

HRID 478844 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:11][CH:12]([C:18]([CH3:20])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CC(C)=O>[ClH:11].[N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]=1[S:1][CH:12]([C:18]([CH3:20])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 178527775HCID 178527775, compound

Product 1

HCID 70027810HCID 70027810, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Acetone (1.5 L) solution of 2-mercaptobenzoimidazole (150 g) and ethyl 2-chloroacetoacetate (247 g) was heated under reflux for 5 hours. The reaction solution was cooled to room temperature, and then the resulting precipitate was collected by filtration to obtain ethyl 2-[(benzoimidazol-2-yl)thio]acetoacetate hydrochloride (303 g) as colorless crystals. The thus obtained crystals (45 g) were dissolved in DMF (200 ml), and the solution was mixed with Py (32 ml) and acetic acid formic acid anhydride (35 g) and stirred for 3 hours while heating at 100° C. After cooling, the reaction solution was poured into water, and the resulting precipitate was collected by filtration and washed with water. The thus obtained solid was dried under a reduced pressure, purified by a column chromatography (eluent; CHCl3) and then recrystallized from EtOAc/Hex to obtain the title compound (22 g).

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-859a68b1e26b4343b10771e079e93ffc
Source dataset
uspto-grants-2003_11
Patent number
US06642264B1

Reaction notes

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