Benzimidazole → 1-Benzyl-1H-benzimidazole

HRID 1492653Notes

Reaction equation

HRID 1492653 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[CH:10]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:2]1([CH2:1][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 5633471-Benzyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To benzyl chloride (13 g, 0.103 mol), 1H-benzimidazole (11.81 g, 0.10 mol), K2CO3 (60 g, 0.434 mol) was added acetonitrile (200 mL) and the mixture was stirred and heated under reflux for 3 h, filtered hot, and washed with hot CH3CN (100 mL). The solvent of the filtrate was evaporated and the residual mass recrystallized as needles (16.5 g, 79%): mp 119°-120° C. (benzene) (lit1 mp 105° C.); 1H NMR (270 MHz, CDCl3) δ5.40 (s, 2H, CH2), 7.20-7.41 (m, 8H), 7.85-7.89 (m, 1H), 8.02 (s, 1H, NCHN); IR (CDCl3) 3093 (w), 3065 (w), 3037 (w), 2929 (w), 1615 (w), 1496 (s), 1456, 1385 (w), 1361, 1331, 1285, 1261, 1204, 1181, 1007 (w), 963 (w), 947 (w) cm1. MS (EI) m/e 208 (M+, 57.8), 91 (100); Anal. Calcd for C14H22N2 (208.26): C, 80.74; H, 5.81; N, 13.45; Found: C, 80.70; H, 6.02; N, 13.31.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. filtrationfiltered hot
  4. washwashed with hot CH3CN (100 mL)
  5. customThe solvent of the filtrate was evaporated
  6. customthe residual mass recrystallized as needles (16.5 g, 79%)

Sources & evidence

ORD record
ord-3daf03abad164e3f8c262e81ae3cd3ce
Source dataset
uspto-grants-1994_12
Patent number
US05374701

Reaction notes

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