Water → HCID 19972453, compound

HRID 1452290Notes

Reaction equation

HRID 1452290 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1.Br[CH2:23][CH2:24][Cl:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][N:2]([CH2:3][C:4]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH2:23][CH2:24][Cl:25]

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 19972641HCID 19972641, compound

Product 1

HCID 19972453HCID 19972453, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 22 g of Intermediate XX, 66 ml of 1-bromo-2-chloroethane and 11 g of anhydrous potassium carbonate in 88 ml of dimethylformamide was stirred at 20°-25° C. for 12 hours. The reaction mixture was then poured into 600 ml of water and extracted with dichloromethane. The organic layer was washed with water, dried on anhydrous sodium sulfate and acidified with ethanolic hydrogen chloride. The solvent and the excess 1-bromo-2-chloroethane were distilled off in vacuo at 70°-80° C. The residue was taken up in cold 1N aqueous sodium hydroxide solution and extracted with dichloromethane. The organic solution was washed with water, dried on anhydrous sodium sulfate and evaporated to dryness in vacuo at 25°-30° C. The crude title product was purified by flash chromatography on silica gel, eluting with ethyl acetate:petroleum ether (7:3), to give 18 g of the title compound melting at 118°-120° C. after crystallization from ethanol.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried on anhydrous sodium sulfate
  4. distillationThe solvent and the excess 1-bromo-2-chloroethane were distilled off in vacuo at 70°-80° C
  5. extractionextracted with dichloromethane
  6. washThe organic solution was washed with water
  7. dry with materialdried on anhydrous sodium sulfate
  8. customevaporated to dryness in vacuo at 25°-30° C
  9. customThe crude title product was purified by flash chromatography on silica gel
  10. washeluting with ethyl acetate:petroleum ether (7:3)

Sources & evidence

ORD record
ord-25b07c4d2bf543df8f9e8b35a53ccb05
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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