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

HRID 1489250ノート

反応式

HRID 1489250 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-75705c6628e74d6b8dd7d8dfc7c60103
出典データセット
uspto-grants-1997_10
特許番号
US05677319

反応ノート

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