Acetyl chloride → HCID 67165879, compound

HRID 878842Notes

Reaction equation

HRID 878842 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36].C(OCC)(=O)C>ClCCl>[C:35]([NH:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67163670HCID 67163670, compound

Product 1

HCID 67165879HCID 67165879, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a solution of 0.20 g of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid amide and 0.12 g of triethylamine in 5 mL of dichloromethane, 0.05 g of acetyl chloride was added under cooling with ice and with stirring, and stirred at room temperature for 40 minutes. After the completion of the reaction, 10 mL of ethyl acetate was added in the reaction mixture, and washed with 10 mL of water, 10 mL of saturated sodium hydrogen carbonate aqueous solution, and then 10 mL of saturated ammonium chloride aqueous solution in that order. The organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.21 g of the crude aimed product as yellow crystal. The resulting product was used as such without purification for the next step.

Workup

  1. temperatureunder cooling with ice
  2. stirringstirred at room temperature for 40 minutes
  3. additionwas added in the reaction mixture
  4. washwashed with 10 mL of water, 10 mL of saturated sodium hydrogen carbonate aqueous solution
  5. dry with materialdried over saturated sodium chloride aqueous solution
  6. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f6704a2735ba48f1a0982848f05ca3d7
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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