Water → 5-(1H-Benzimidazol-2-ylmethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one

HRID 69048Notes

Reaction equation

HRID 69048 reaction equation
O[CH:2](O)[CH2:3][N:4]1[CH:9]=[CH:8][C:7]2[O:10][C:11]([CH3:13])=[CH:12][C:6]=2[C:5]1=[O:14].[C:16]1([NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22].S([O-])(O)=O.[Na+].O>C(O)C>[NH:22]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:23]=[C:2]1[CH2:3][N:4]1[CH:9]=[CH:8][C:7]2[O:10][C:11]([CH3:13])=[CH:12][C:6]=2[C:5]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7243O-PhenylenediamineHCID 23665763Sodium BisulfiteHCID 669600005-(2,2-Dihydroxyethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one

Product 1

HCID 669600755-(1H-Benzimidazol-2-ylmethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-oneYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2,2-Dihydroxyethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one (2.1 g) and o-phenylenediamine (1.1 g) were suspended in ethanol (20 ml). Sodium hydrogensulfite (5.2 g) was added, and the mixture was heated and stirred overnight under reflux. The reaction mixture was cooled to room temperature. Water was added thereto and the precipitated insoluble matter was separated, washed with water, and dried to give the title compound (2.25 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customthe precipitated insoluble matter was separated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7c7b5776697944f99bb7978ddec20769
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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