Ammonium Chloride → 2-(3,4-Diethoxyphenyl)-4-[1-hydroxy-1-(3,4-dimethoxyphenyl)methyl]thiazole

HRID 263582노트

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HRID 263582 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:24]2[S:25][CH:26]=[C:27]([CH:29]=[O:30])[N:28]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH3:23])[CH3:13].[Cl-].[NH4+]>O1CCCC1>[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:24]2[S:25][CH:26]=[C:27]([CH:29]([OH:30])[C:2]3[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=3)[N:28]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH3:23])[CH3:13]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 187072072-(3,4-Diethoxyphenyl)-4-formylthiazole

생성물 1

HCID 187071262-(3,4-Diethoxyphenyl)-4-[1-hydroxy-1-(3,4-dimethoxyphenyl)methyl]thiazole수율 48.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

60 ml of a tetrahydrofuran solution of a Grignard reagent prepared from 2.4 g of 1-bromo-3,4-dimethoxybenzene was stirred with ice-cooling. Thereto was added 20 ml of a tetrahydrofuran solution of 3 g of 2-(3,4-diethoxyphenyl)-4-formylthiazole. The mixture was stirred at the same temperature for 1 hour and at room temperature for 3 hours. 10 ml of a saturated aqueous ammonium chloride solution was added. The solvent was removed by distillation. The residue was extracted with 100 ml of chloroform. The extract was washed with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution, and dried. The solvent was removed by distillation. The residue was purified by silica gel column chromatography (elutant: dichloromethane/acetone=99/1 by v/v) and recrystallized from diethyl ether to obtain 2.2 g of 2-(3,4-diethoxyphenyl)-4-[1-hydroxy-1-(3,4-dimethoxyphenyl)methyl]thiazole

후처리

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour and at room temperature for 3 hours
  3. customThe solvent was removed by distillation
  4. extractionThe residue was extracted with 100 ml of chloroform
  5. washThe extract was washed with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution
  6. customdried
  7. customThe solvent was removed by distillation
  8. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/acetone=99/1 by v/v)
  9. customrecrystallized from diethyl ether

출처 및 근거

ORD 기록
ord-c78d6bb97439415a99b0bf999feea550
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643932

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