Formic Acid → HCID 178424047, compound

HRID 344720Notes

Reaction equation

HRID 344720 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH2:18])=[C:11]([NH2:17])[C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19](O)=O>>[CH2:1]([O:8][C:9]1[C:10]2[N:18]=[CH:19][NH:17][C:11]=2[C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 53992690HCID 53992690, compound

Product 1

HCID 178424047HCID 178424047, compoundYield 61%

Procedure

A mixture of 2.50 g (10.3 mmols) of 3-benzyloxy-4,6-dimethyl-1,2-phenylenediamine [J. Med. Chem., 30, 2216 (1987)]and 20 ml of formic acid was heated under reflux for 30 minutes. The mixture was concentrated under reduced pressure, and then an aqueous saturated sodium bicarbonate solution was added to the residue followed by extraction of the solution with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/ methanol =40/1) to afford 1.59 g (yield: 61%) of 7-benzyloxy-4,6-dimethylbenzimidazole.

Workup

  1. temperatureunder reflux for 30 minutes
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionan aqueous saturated sodium bicarbonate solution was added to the residue
  4. extractionfollowed by extraction of the solution with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform/ methanol =40/1)

Sources & evidence

ORD record
ord-023524bccad84078ba17d672c0dba8c0
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

Loading…