Benzyl Chloride → 1-Benzyl-2-(benzylsulfanyl)-6-methyl-1H-benzimidazole

HRID 495228Notes

Reaction equation

HRID 495228 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([N:3]1[C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:11][C:9]1[CH:10]=[CH:4][CH:5]=[CH:7][CH:8]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 178423448HCID 178423448, compound

Product 1

HCID 666282781-Benzyl-2-(benzylsulfanyl)-6-methyl-1H-benzimidazoleYield 166.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 2.0 g 2-mercapto-5-methylbenzimidazole, 4.2 g potassium carbonate, 30 ml N,N-dimethylformamide and 3.9 g benzyl chloride. The reaction mixture was heated to 60 C for 16 hours, then cooled to 50 C and quenched with 60 ml water and cooled to 5 C. The solid was filtered and washed with water and then recrystallized by dissolving in 50 ml hot acetonitrile and adding 10 ml of water. After cooling to 5 C, the product was filtered, washed and dried resulting in 3.5 g white solid as a mixture of the 5-methyl and 6-methyl isomers.

Workup

  1. temperatureThe reaction mixture was heated to 60 C for 16 hours
  2. temperaturecooled to 50 C
  3. customquenched with 60 ml water
  4. temperaturecooled to 5 C
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customrecrystallized
  8. dissolutionby dissolving in 50 ml hot acetonitrile
  9. additionadding 10 ml of water
  10. temperatureAfter cooling to 5 C
  11. filtrationthe product was filtered
  12. washwashed
  13. customdried

Sources & evidence

ORD record
ord-0ad0bf33e03f43c29d7c6c17ce4df4be
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Reaction notes

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