Sodium hydride → HCID 54415840, compound

HRID 991218Notes

Reaction equation

HRID 991218 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([NH:10][C:22]([CH:19]2[CH2:21][CH2:20]2)=[O:23])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 77637Cyclopropanecarbonyl chlorideHCID 784202,2-DiphenylacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 54415840HCID 54415840, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (0° C.) solution of 2,2-diphenylacetamide (500 mg, 2.36 mmol) in THF (20 ml) was added sodium hydride (95 mg, 2.36 mmol; 60%) and the mixture was stirred at RT for 0.5 h. Then cyclopropanecarboxylic acid chloride (247 mg, 2.36 mmol) dissolved in THF (5 ml) was added dropwise at RT and the solution was stirred at RT for 20 h. The reaction mixture was poured into sat. NaHCO3 solution (50 ml) and extracted with ethyl acetate (2×70 ml). The combined organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated. Further purification by column chromatography (toluene/ethyl acetate 19:1) yielded the product which was recrystallized from ethyl acetate/hexane to give a white solid (133 mg, 20%), m.p. 178° C. and MS: m/e=279 (M+).

Workup

  1. stirringthe mixture was stirred at RT for 0.5 h
  2. additionwas added dropwise at RT
  3. stirringthe solution was stirred at RT for 20 h
  4. extractionextracted with ethyl acetate (2×70 ml)
  5. washThe combined organic layers were washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customFurther purification by column chromatography (toluene/ethyl acetate 19:1)
  9. customyielded the product which
  10. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-811f500ed9274f3eaafac27bedd6658e
Source dataset
uspto-grants-2002_10
Patent number
US06462198B1

Reaction notes

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