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

HRID 8404ノート

反応式

HRID 8404 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-58ca58da0f794be99a415fb53af683dc
出典データセット
uspto-grants-2006_08
特許番号
US07087764B2

反応ノート

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