2-Chloromethylbenzimidazole → HCID 9927050, compound

HRID 861388Notes

Reaction equation

HRID 861388 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Cl[CH2:16][C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CN(C)C=O>[CH3:1][C:2]1[O:6][C:5](/[CH:7]=[CH:8]/[C:9]2[CH2:10][CH2:11][N:12]([CH2:16][C:17]3[NH:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 785712-ChloromethylbenzimidazoleHCID 54444704HCID 54444704, compound

Product 1

HCID 9927050HCID 9927050, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[2-(5-methylfuran-2-yl)ethenyl]pyridine (1.0 g, 5.41 mmol) in anhydrous dimethylformarnide (20 ml) was treated with 2-chloromethylbenzimidazole (1.0 g, 5.95 mmol). The reaction was stirred at reflux for two hours. The solvent was evaporated and the residue redissolved in absolute ethanol (50 ml). Sodium borehydride (251 mg, 6.76 mmol) was added and the mixture stirred at reflux for 40 mins. The solvent was evaporated and the residue partitioned between dichloromethane and water. The organic phase was separated, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel using 97:3:1 dichloromethane/methanol/ammonia as eluant to afford the title compound (500 mg, 30%) as a pale lemon solid, m.p. 191°-193° C.; (Found: C, 75.33; H, 6.32; N, 13.17. C20H21N3O requires C, 75.21; H, 6.63; N, 13.16); δH (DMSO-d6) 2.25-2.35 (5H, m, CH3 and tetrahydropyridinyl CH2), 2.66 (2H, t, J 5.7 Hz, tetrahydropyridinyl CH2), 3.14-3.20 (2H, m, tetrahydropyridinyl CH2), 3.82 (2H, s, NCH2Ar), 5.82-5.88 (1H, m, tetrahydropyridinyl CH), 6.06-6.10 (1H, m, furan 4-H), 6.22-6.30 (2H, m, CH=CH and furan 3-H), 6.58 (1H, d, J 16.1 Hz, CH=CH), 7.05-7.20 (2H, m, 5-H and 6-H), 7.38-7.60 (2H, m, 4-H and 7-H), and 12.29 (1H, s, NH); m/z (CI+, NH3) 320 (M+1)+.

Workup

  1. temperatureat reflux for two hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue redissolved in absolute ethanol (50 ml)
  4. additionwas added
  5. stirringthe mixture stirred
  6. temperatureat reflux for 40 mins
  7. customThe solvent was evaporated
  8. customthe residue partitioned between dichloromethane and water
  9. customThe organic phase was separated
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe residue was chromatographed on silica gel using 97:3:1 dichloromethane/methanol/ammonia as eluant

Sources & evidence

ORD record
ord-e7b66b7fe58f4d86b8e5614202b52965
Source dataset
uspto-grants-1998_02
Patent number
US05714498

Reaction notes

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