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

HRID 1421966Notes

Reaction equation

HRID 1421966 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-a42e387aa7654072be8266a981854cd5
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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