Ethylenethiourea → 1-[1-(3,4-Dichlorophenyl)cyclobutyl]-2-(2-imidazolin-2-ylthio)ethanone hydrobromide

HRID 635338Notes

Reaction equation

HRID 635338 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[S:6].[Br:7][CH2:8][C:9]([C:11]1([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[CH2:14][CH2:13][CH2:12]1)=[O:10]>CC(C)=O>[BrH:7].[Cl:22][C:17]1[CH:16]=[C:15]([C:11]2([C:9](=[O:10])[CH2:8][S:6][C:2]3[NH:1][CH2:5][CH2:4][N:3]=3)[CH2:14][CH2:13][CH2:12]2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

4

Reactant 2

HCID 2723650EthylenethioureaHCID 212584722-Bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethan-1-one

Product 1

HCID 212585071-[1-(3,4-Dichlorophenyl)cyclobutyl]-2-(2-imidazolin-2-ylthio)ethanone hydrobromideYield 87.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of imidazolidine-2-thione (4.5 g) in acetone (750 ml ) was added to a solution of 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone (15 g) in acetone (125 ml), then the stirred mixture was heated under reflux for 10 minutes, and allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ethanol (50 ml) and dried in vacuo at 60° C. for 4 hours to give 1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-(2-imidazolin-2-ylthio)ethanone hydrobromide as a white solid (16.3 g), m.p. 156-158° C.

Workup

  1. temperaturethe stirred mixture was heated
  2. temperatureunder reflux for 10 minutes
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ethanol (50 ml)
  5. customdried in vacuo at 60° C. for 4 hours

Sources & evidence

ORD record
ord-74e0418616e94647b676dce864778aaf
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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