Formaldehyde → HCID 17027847, compound

HRID 353009Notes

Reaction equation

HRID 353009 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH3:16])=[CH:4][CH:3]=1.[CH2:19]=[O:20]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:16][CH2:19][OH:20])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 7438921H-Benzimidazole, 2-methyl-1-[(4-methylphenyl)methyl]-

Product 1

HCID 17027847HCID 17027847, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

Next, 1-(4-methylbenzyl)-2-(2-hydroxyethyl)benzimidazole was prepared. A mixture of 1-(4-methylbenzyl)-2-methylbenzimidazole (5.1 g, 21 mmol), formaldehyde (82 mmol as 6.7 g of the 37% aqueous solution), and 6.5 g of pyridine were stirred magnetically and heated to 90° C. After 24 h, the mixture was cooled to ambient and concentrated at reduced pressure to deposit a tan oil. The product was purified by flash chromatography (silica gel, 75% dichloromcthane/25% ether), followed by recrystallization from a mixture of 15 mL of methanol plus 10 mL of water. The product was obtained as 1.5 g (41%) of a white solid. 1H NMR (CDCl3)δ 2.31 (s, 3H), 2.99 (t, J=5.4, 2H), 4.12 (t, J=5.4, 2H), 4.4 (br s, 1H), 5.29 (s, 2H), 6.94 (d, J=8.0, 2H), 7.10 (d, J=7.9, 2H), 7.25 (m, 3H), 7.73 (m, 1H). ES−MS m/e 267+ (M+1).

Workup

  1. temperaturethe mixture was cooled to ambient and
  2. concentrationconcentrated at reduced pressure
  3. customThe product was purified by flash chromatography (silica gel, 75% dichloromcthane/25% ether)
  4. customfollowed by recrystallization from a mixture of 15 mL of methanol plus 10 mL of water

Sources & evidence

ORD record
ord-956e22521e914ac083622480656e03b9
Source dataset
uspto-grants-2004_06
Patent number
US06749977B1

Reaction notes

Loading…