Methanol → HCID 178504696, compound

HRID 2231102Notes

Reaction equation

HRID 2231102 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([CH2:13][OH:14])=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18](SC)=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.O[O:24][S:25]([O-:27])=O.[K+].CO.O1CCC[CH2:32]1>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([CH2:13][OH:14])[NH:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18]([S:25]([CH3:32])(=[O:27])=[O:24])=[CH:17][CH:16]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 536747975-(4-fluorophenyl)-2-hydroxymethyl-4-(4-methylthiophenyl)-1H-imidazole

Product 1

HCID 178504696HCID 178504696, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of 2-hydroxymethyl-imidazole from step 4 (150 mg, 0.4 mmol), OXONE®(450 mg, excess), water (2 ml), methanol (5 ml) and tetrahydrofuran (3 ml) was stirred at 25° C. for 2 hours. The reaction mixture was diluted with water (20 ml) and extracted with methylene chloride. After removal of solvent, the crude material was recrystallized from toluene to give 80 mg (70%) of 4-(4-fluorophenyl)-2-hydroxymethyl-5-(4-methylsulfonylphenyl)-1H-imidazole: m.p. 115-117° C. Anal. Calc'd. for C17H15N2O3FS. H2O: C, 56.03; 4.70; N, 7.69; S, 8.80. Found: C, 56.02; H, 4.64; N, 7.45; S, 8.90.

Workup

  1. extractionextracted with methylene chloride
  2. customAfter removal of solvent
  3. customthe crude material was recrystallized from toluene

Sources & evidence

ORD record
ord-5428fadb1a6a4e63b72243852f26382f
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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