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

HRID 8406노트

반응식

HRID 8406 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1b1cbabccb3541bf91aad69e89164acf
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087764B2

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