Allyl chloride → Methanone, phenyl[2-(2-propen-1-ylthio)-1H-benzimidazol-6-yl]-, hydrochloride (1:1)

HRID 1194328Notes

Reaction equation

HRID 1194328 reaction equation
[C:1]([C:9]1[CH:18]=[CH:17][C:12]2=[N:13][C:14](=[S:16])[N:15]=[C:11]2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([Cl:22])[CH:20]=[CH2:21]>C(O)C>[ClH:22].[C:2]1([C:1]([C:9]2[CH:18]=[CH:17][C:12]3[N:13]=[C:14]([S:16][CH2:21][CH:20]=[CH2:19])[NH:15][C:11]=3[CH:10]=2)=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7850Allyl chloride2×HCID 21269541HCID 21269541, compound

Product 1

HCID 21269521Methanone, phenyl[2-(2-propen-1-ylthio)-1H-benzimidazol-6-yl]-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.55 g (25.76 mmoles) of 5-benzoyl-benzimidazol-2-thione, 2.45 ml of allyl chloride and 40 ml of ethanol are refluxed for 20 hours, thereafter further 2.45 ml of allyl chloride are added and the mixture is refluxed for further 5 hours. The product precipitates upon cooling. The weight (86.7%). M.p.: 182°-183° C. (after recrystallization from isopropanol)

Workup

  1. temperaturethe mixture is refluxed for further 5 hours
  2. customThe product precipitates
  3. temperatureupon cooling
  4. customM.p.: 182°-183° C. (after recrystallization from isopropanol)

Sources & evidence

ORD record
ord-d75aec393e1c4c61b1914923ebafe635
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

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