Dimethylformamide dimethyl acetal → 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl]-N-[(dimethylamino)methylene]-2-methylbenzamide

HRID 1187980Notes

Reaction equation

HRID 1187980 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CO[CH:30](OC)[N:31]([CH3:33])[CH3:32]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([N:20]=[CH:30][N:31]([CH3:33])[CH3:32])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 667845734-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide

Product 1

HCID 547675024-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl]-N-[(dimethylamino)methylene]-2-methylbenzamide

Conditions

Temperature
120 °C

Procedure

A mixture of 6.0 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide synthesized in Step 1 of Synthetic Example 19 and 50 mL of N,N-dimethylformamide dimethylacetal were stirred at 120° C. for 1.5 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure. The residual solid was washed with ethyl acetate-hexane mixture (1:20) to obtain 6.2 g of the aimed product as pale yellow crystal.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. washThe residual solid was washed with ethyl acetate-hexane mixture (1:20)

Sources & evidence

ORD record
ord-ed70697296064a129e494214c7663224
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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