2-Bromo-1-[1-(4-Chlorophenyl)cyclobutyl]ethanone → 1-[1-(4-Chlorophenyl)cyclobutyl]-2-(3,4,5,6-tetrahydropyrimidin-2-ylthio)ethanone hydrobromide

HRID 635342Notes

Reaction equation

HRID 635342 reaction equation
[Br:1][CH2:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[N:16]1[CH2:21][CH2:20][CH2:19][NH:18][C:17]=1[SH:22]>CC(C)=O>[BrH:1].[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2([C:3](=[O:4])[CH2:2][S:22][C:17]3[NH:18][CH2:19][CH2:20][CH2:21][N:16]=3)[CH2:8][CH2:7][CH2:6]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 219019212-Bromo-1-[1-(4-Chlorophenyl)cyclobutyl]ethanoneHCID 178527864HCID 178527864, compound

Product 1

HCID 212583641-[1-(4-Chlorophenyl)cyclobutyl]-2-(3,4,5,6-tetrahydropyrimidin-2-ylthio)ethanone hydrobromideYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 2-bromo-1-[1-(4-chlorophenyl)cyclobutyl]ethanone (2.9 g) in acetone (25 ml) was added to a solution of 3,4,5,6-tetrahydropyrimidine-2-thiol (1.2 g) in acetone (150 ml), then the mixture was heated under reflux for 1 hour, and allowed to cool to ambient temperature. The resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 1-[1-(4-chlorophenyl)cyclobutyl]-2-(3,4,5,6-tetrahydropyrimidin-2-ylthio)ethanone hydrobromide as a white solid (3.5 g), m.p. 205° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. filtrationThe resulting solid was collected by filtration
  4. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-b2703ce6696c44799f310dd2f2dbb392
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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