Methyl Isobutyl Ketone → 1-(3-chloropropyl)-2-(methylthio)-1H-benzimidazole

HRID 258846

Reaction equation

HRID 258846 reaction equation
[CH3:1][S:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.Br[CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[Cl:16][CH2:15][CH2:14][CH2:13][N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=[C:3]1[S:2][CH3:1]

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 80061-Bromo-3-chloropropaneHCID 10340Sodium CarbonateHCID 235392-(Methylthio)benzimidazole

Product 1

HCID 135640281-(3-chloropropyl)-2-(methylthio)-1H-benzimidazoleYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.2 parts of 2-(methylthio)-1H-benzimidazole, 16 parts of 1-bromo-3-chloropropane, 5.3 parts of sodium carbonate and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 44 hours. After cooling, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is stirred in 2,2'-oxybispropane. The unreacted starting material is filtered off and the filtrate is evaporated, yielding 6 parts (50%) of 1-(3-chloropropyl)-2-(methylthio)-1H-benzimidazole as an oily residue.

Workup

  1. temperaturerefluxed for 44 hours
  2. temperatureAfter cooling
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe residue is stirred in 2,2'-oxybispropane
  8. filtrationis filtered off
  9. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-694125e3bfad4e168ff476ac012846e7
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Linked notes

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