Dimethylformamide → HCID 22765908, compound

HRID 1111932Notes

Reaction equation

HRID 1111932 reaction equation
ClC(O[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[Br-:11].[Na+].CO.O.[CH3:16][N:17]([CH3:20])[CH:18]=[O:19]>>[Br-:11].[C:5]1([C:18]([N:17]([CH3:20])[CH3:16])=[O:19])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 15891Phenyl chloroformateHCID 253881Sodium BromideHCID 22242641Methanol--water (1/1)

Product 1

HCID 22765908HCID 22765908, compound

Conditions

Temperature
0 °C

Procedure

Phenyl N,N-dimethylformamide bromide was prepared by dropwise addition of phenyl chloroformate (6.5 ml; 50 mmol) to a stirred solution of sodium bromide (5.14 g; 50 mmol) in dimethylformamide at 0°-5° C. Sodium chloride precipitated, and the resulting suspension was stirred at 0°-5° C. for 4 hours and then at room temperature overnight. The mixture was cooled to 0° C. and 16-deacetoxy-16β-(acetylthio)fusidic acid acetoxymethyl ester (6.07 g; 10 mmol) was added with stirring. After stirring at 0°-5° C. for 4 hours, the mixture was left at room temperature for a further 4 days. On dilution of the stirred reaction mixture with methanol-water 1:1 (75 ml) an oily product precipitated, which was washed repeatedly by decantation with methanol-water 1:1 and finally taken up in ether, dried, and evaporated in vacuo. The amorphous residue thus obtained was purified by dry column chromatography on silica gel (petroleum ether-ethyl acetate 85:15) to give the desired compound as a colourless foam.

Workup

  1. customSodium chloride precipitated
  2. customat room temperature
  3. customovernight
  4. stirringwith stirring
  5. stirringAfter stirring at 0°-5° C. for 4 hours
  6. waitthe mixture was left at room temperature for a further 4 days
  7. customprecipitated
  8. washwhich was washed repeatedly by decantation with methanol-water 1:1
  9. customdried
  10. customevaporated in vacuo
  11. customThe amorphous residue thus obtained
  12. customwas purified
  13. customby dry column chromatography on silica gel (petroleum ether-ethyl acetate 85:15)

Sources & evidence

ORD record
ord-97e0a625f9c64beba09efdec33590f85
Source dataset
uspto-grants-1978_10
Patent number
US04119717

Reaction notes

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