Acetyl chloride → HCID 86654453, compound

HRID 552627Notes

Reaction equation

HRID 552627 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([NH:10][C:11](=[O:36])[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH2:22][C:21]([C:27]4[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=4)([C:23]([F:26])([F:25])[F:24])[O:20][N:19]=3)=[CH:14][C:13]=2[CH3:35])[CH:7]=[CH:6][CH:5]=1.[H][H].[C:39](Cl)(=[O:41])[CH3:40]>CN(C)C=O>[C:39]([N:10]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:3])[N:9]=1)[C:11](=[O:36])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:22][C:21]([C:27]3[CH:28]=[C:29]([Cl:34])[CH:30]=[C:31]([Cl:33])[CH:32]=3)([C:23]([F:25])([F:26])[F:24])[O:20][N:19]=2)=[CH:14][C:13]=1[CH3:35])(=[O:41])[CH3:40]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 86654452HCID 86654452, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86654453HCID 86654453, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a suspension of 0.10 g of 55% oily sodium hydride suspended in 15 mL of N,N-dimethylformamide, a solution of 0.30 g of N-(6-chloro-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amide in 5 mL of N,N-dimethylformamide was added under cooling with ice and with stirring, and stirred at the same temperature for 10 minutes. After ceasing the generation of hydrogen gas, 0.30 g of acetyl chloride was added, ice bath was removed and continued to stir further for 5 minutes. After the completion of the reaction, the reaction mixture was poured in 20 mL of ice water, extracted with ethyl acetate (50 mL×1), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.11 g of the aimed product as colorless resinous substance.

Workup

  1. temperatureunder cooling with ice
  2. stirringstirred at the same temperature for 10 minutes
  3. additionwas added
  4. customice bath was removed
  5. stirringto stir further for 5 minutes
  6. customAfter the completion of the reaction
  7. extractionextracted with ethyl acetate (50 mL×1)
  8. dry with materialdried over saturated sodium chloride aqueous solution
  9. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
  10. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-21163f05057f4075832a68aeac2b9383
Source dataset
uspto-grants-2011_05
Patent number
US07951828B1

Reaction notes

Loading…