Water → 2-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazole

HRID 8404Notes

Reaction equation

HRID 8404 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:11]([C:18]2[CH:23]=[CH:22]N=CC=2)[CH:12]=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:26]=[C:27]([S:32]Cl)[CH:28]=[C:29]([Cl:31])[CH:30]=1.[CH2:34]([N:36](CC)[CH2:37]C)[CH3:35].O>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH2:18][C:23]2[CH:22]=[CH:37][N:36]=[CH:34][CH:35]=2)[C:12]([S:32][C:27]2[CH:26]=[C:25]([Cl:24])[CH:30]=[C:29]([Cl:31])[CH:28]=2)=[C:13]([CH:15]([CH3:16])[CH3:17])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 101305733,5-Dichlorobenzenesulfenyl chlorideHCID 220157572-Benzyloxymethyl-4-isopropyl-1-(pyridin-4-yl)-1H-imidazole

Product 1

HCID 98487522-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazoleYield 81.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

2-Benzyloxymethyl-4-isopropyl-1-(pyridin-4-yl)-1H-imidazole (5) (10.0 g, 31.1 mmol) was dissolved in toluene (50 ml). The solution was added dropwise to a solution of 3,5-dichlorobenzenesulfenyl chloride (3) (8.0 g, 37.05 mmol) in toluene (24.7 g) under ice-cooling for 30 minutes. To the mixture was added dropwise triethylamine (3.5 g, 34.6 mmol) under ice-cooling for 1 hour and the mixture was stirred at the same temperature for 1.5 hours. To the mixture was added water (25 ml) and toluene layer was separated. The toluene layer was washed with water (25 ml) and each aqueous layer was extracted with toluene (10 ml). The toluene layer was collected, concentrated under reduced pressure to give oily product, which was crystallized with diisopropyl ether 50 ml, filtered and dried to yield the objective (6) (12.6 g) as a pale yellow crystal. Yield 81.3%.

Workup

  1. temperaturecooling for 30 minutes
  2. temperaturecooling for 1 hour
  3. customwas separated
  4. washThe toluene layer was washed with water (25 ml)
  5. extractioneach aqueous layer was extracted with toluene (10 ml)
  6. customThe toluene layer was collected
  7. concentrationconcentrated under reduced pressure
  8. customto give oily product, which
  9. customwas crystallized with diisopropyl ether 50 ml
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-58ca58da0f794be99a415fb53af683dc
Source dataset
uspto-grants-2006_08
Patent number
US07087764B2

Reaction notes

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