Water → HCID 22282192, compound

HRID 2245324Notes

Reaction equation

HRID 2245324 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17]([NH2:24])=[CH:18][CH:19]=[C:20]([O:22][CH3:23])[CH:21]=2)=[CH:11][CH:10]=1.O.C(OCC)(=O)C>OS([O-])=O.[Na+].C(O)C>[CH3:23][O:22][C:20]1[CH:19]=[CH:18][C:17]2[N:24]=[C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)[N:15]([C:12]3[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=3)[C:16]=2[CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 681353-ThiophenecarboxaldehydeHCID 80456514HCID 80456514, compound

Product 1

HCID 22282192HCID 22282192, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23665763Sodium BisulfiteSolvent

Procedure

7.48 g of thiophene-3-aldehyde was stirred in 65 ml of 40% NaHSO3 solution for two hours. After 15 g of N2-(4-fluorophenyl)-4-methoxybenzene-1,2-diamine in 50 ml of ethanol was added, it was boiled for 4 hours, and stirring was continued overnight. The batch was dispersed between water and ethyl acetate, and the organic phase was washed with water. After drying on sodium sulfate and concentration by evaporation of the filtrate, 18.1 g of crude 6-methoxy-1-(4-fluorophenyl)-2-(3-thienyl)-1H-benzimidazole is obtained.

Workup

  1. waitwas continued overnight
  2. washthe organic phase was washed with water
  3. customAfter drying on sodium sulfate and concentration by evaporation of the filtrate

Sources & evidence

ORD record
ord-228adb8d0bcd4b81981f9ffd7b048209
Source dataset
uspto-grants-2010_03
Patent number
US07683081B2

Reaction notes

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