Methanol → HCID 19792172, compound

HRID 653710Notes

Reaction equation

HRID 653710 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[C:8]2[C:25]([C:29](OC)=[O:30])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].CO>O1CCCC1>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:15][CH:16]=2)[C:8]2[C:25]([CH2:29][OH:30])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 18693194Methyl 2-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate

Product 1

HCID 19792172HCID 19792172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate (10 g) and NaBH. (2.2 g) in tetrahydrofuran (100 ml) was added dropwise methanol (19 ml) during 80 minutes. The mixture was heated for 27 further hours under reflux, and the reaction mixture was concentrated to dryness. To the concentrate was added water, which was neutralized with conc. HCl. Crystals thus separated were collected by filtration. Recrystallization from methanol afforded colorless needles (8.8 g, 93%), m.p. 203°-204° C.

Workup

  1. temperatureThe mixture was heated for 27 further hours
  2. temperatureunder reflux
  3. concentrationthe reaction mixture was concentrated to dryness
  4. additionTo the concentrate was added water, which
  5. customCrystals thus separated
  6. filtrationwere collected by filtration
  7. customRecrystallization from methanol afforded colorless needles (8.8 g, 93%), m.p. 203°-204° C.

Sources & evidence

ORD record
ord-a6e06ebe3c2344b990394083d2732246
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

Loading…