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

HRID 8406ノート

反応式

HRID 8406 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]Cl)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:11]([O:14][CH2:15][C:16]1[N:17]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:18]=[C:19]([CH:21]([CH3:23])[CH3:22])[N:20]=1)(=[O:13])[CH3:12].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(#N)C>[C:11]([O:14][CH2:15][C:16]1[N:17]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[C:18]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:19]([CH:21]([CH3:23])[CH3:22])[N:20]=1)(=[O:13])[CH3:12]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 101305733,5-Dichlorobenzenesulfenyl chlorideHCID 154583312-Acetyloxymethyl-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazole

生成物 1

HCID 98465722-Acetyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-yl)methyl-1H-imidazole収率 82%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

To a solution of the compound (3) (0.97 g, 4.5 mmol) in toluene (1.88 g) was added dropwise a solution of the compound (10a) (0.87 g, 3.2 mmol) in acetonitrile (4 ml) under ice-cooling for 30 minutes. A solution of triethylamine (0.46 g, 4.5 mmol) in acetonitrile (0.5 ml) was added dropwise thereto for 15 minutes, and the mixture was stirred under ice-cooling for 2 hours. The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate. The extract was washed with water, concentrated under reduced pressure and purified by column chromatography on silica gel (elution ethyl acetate) to yield the objective (11) (1.17 g) as a crystal. Yield 82%. Mp 133–135° C.

後処理

  1. temperaturecooling for 30 minutes
  2. temperaturecooling for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography on silica gel (elution ethyl acetate)

出典と根拠

ORDレコード
ord-1b1cbabccb3541bf91aad69e89164acf
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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