Formaldehyde → 1H-Benzimidazole-1-methanol

HRID 897967Notes

Reaction equation

HRID 897967 reaction equation
[CH2:1]=[O:2].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1>C1COCC1>[N:3]1([CH2:1][OH:2])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 5798Benzimidazole

Product 1

HCID 1464891H-Benzimidazole-1-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Formaldehyde (37% in water, 1 mL, 13.3 mmol) was added to a solution of 1H-benzo[d]imidazole (1.57 g, 13.3 mmol) in THF (60 ml). After 10 minutes, the solvent was removed and dried to give 1H-benzo[d]imidazol-1-ylmethanol as a brown solid which was used without any further purification. 1H NMR (DMSO-d6) δ 5.60 (d, J=7.09 Hz, 2H), 6.70 (m, 1H), 7.25 (m, 2H), 7.65 (d, J=9.13 Hz, 2H), 8.26 (s, 1H).

Workup

  1. customthe solvent was removed
  2. customdried

Sources & evidence

ORD record
ord-b9c5b809f96341168a4c6f374a33ca3d
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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