Formaldehyde → (1-methyl-1H-1,3-benzodiazol-2-yl)methanol

HRID 1384580Notes

Reaction equation

HRID 1384580 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[CH2:11]=[O:12]>>[OH:12][CH2:11][C:3]1[N:2]([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 712Formaldehyde2×HCID 958901H-Benzimidazole, 1-methyl-

Product 1

HCID 344177(1-methyl-1H-1,3-benzodiazol-2-yl)methanolYield 45%

Procedure

A solution of 1-methylbenzimidazole (2.5 g, 19 mmol), (J. Chem. Soc. 1929, 2820-2828), and paraformaldehyde (2 g) was heated at 165° C. for 30 minutes. Further paraformaldehyde (1 g) was added and heating continued for 2 hours. The mixture was allowed to cool and was purified by column chromatography eluting with methylene chloride, followed by methylene chloride/methanol (95/5) to give 2-hydroxymethyl-1-methylbenzimidazole (1.34 g, 45%). 1H NMR Spectrum: (DMSOd6) 3.84(s, 3H); 4.73(s, 2H); 5.57(br s, 1H); 7.19(t, 1H); 7.25(t, 1H); 7.54(d, 1H); 7.60(d, 1H) MS-ESI: 185 [MNa]+

Workup

  1. temperatureheating
  2. temperatureto cool
  3. customwas purified by column chromatography
  4. washeluting with methylene chloride

Sources & evidence

ORD record
ord-51e86910793d44e7b9ca70c1ea4f6bc2
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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