Water → HCID 178487838, compound

HRID 620827Notes

Reaction equation

HRID 620827 reaction equation
O[N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:5]([CH3:13])[N:4]=[C:3]1[C:14]1[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1.P(OCC)(OCC)OCC.O>CN(C)C=O>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([C:3]2[NH:2][C:6]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)=[C:5]([CH3:13])[N:4]=2)[CH:19]=[CH:18][C:17]=1[S:20][CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 14211343HCID 14211343, compound

Product 1

HCID 178487838HCID 178487838, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-hydroxy-2-(3-methoxy-4-methylthiophenyl)-4-methyl-5-(3-pyridyl)imidazole (0.98 g) in N,N-dimethylformamide (10 ml) was added triethyl phosphite (1.03 ml), and the mixture was stirred at 90° C. for 3 hours. Then the solution was poured into water (60 ml) and stirred at ambient temperature for an hour. The resulting precipitates were filtered, washed with water, and recrystallized from ethanol (6 ml) to give 2-(3-methoxy-4-methylthiophenyl)-4-methyl-5-(3-pyridyl)imidazole (0.58 g).

Workup

  1. stirringstirred at ambient temperature for an hour
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customrecrystallized from ethanol (6 ml)

Sources & evidence

ORD record
ord-37984e10998e4738b364b42033a8dc46
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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