Water → HCID 19972453, compound

HRID 2400170Notes

Reaction equation

HRID 2400170 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 XI, 66 ml of 1-bromo-2-chloroethane and 11 g of anhydrous potassium carbonate in 88 ml of dimethylformamide was stirred at 20°-251° 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 sulphate and acidified with hydrochloric acid in ethanol. The solvent and the excess 1-bromo-2-chloroethane were distilled off in vacuo at 70°-80° C. The residue was taken up in an aqueous 1N sodium hydroxide solution and extracted with dichloromethane. The organic solution was washed with water, dried on anhydrous sodium sulphate and evaporated to dryness in vacuo at 25°-30° C. The crude residue 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 point 118°-120° C. (ethanol).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried on anhydrous sodium sulphate
  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 sulphate
  8. customevaporated to dryness in vacuo at 25°-30° C
  9. customThe crude residue was purified by flash chromatography on silica gel
  10. washeluting with ethyl acetate:petroleum ether (7:3)

Sources & evidence

ORD record
ord-2e1e663345a1490892ec8a2ebbf31ff7
Source dataset
uspto-grants-1995_09
Patent number
US05453518

Reaction notes

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