Hydrochloric Acid → N-Aminomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide hydrochloride

HRID 910395Notes

Reaction equation

HRID 910395 reaction equation
FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.C(C[NH:26][C:27](=[O:52])[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH2:38][C:37]([C:43]3[CH:48]=[C:47]([Cl:49])[CH:46]=[C:45]([Cl:50])[CH:44]=3)([C:39]([F:42])([F:41])[F:40])[O:36][N:35]=2)=[CH:30][C:29]=1[CH3:51])(=O)N.O.Cl.[C:55](#[N:57])C.O>>[ClH:49].[NH2:57][CH2:55][NH:26][C:27](=[O:52])[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH2:38][C:37]([C:43]3[CH:48]=[C:47]([Cl:49])[CH:46]=[C:45]([Cl:50])[CH:44]=3)([C:39]([F:40])([F:41])[F:42])[O:36][N:35]=2)=[CH:30][C:29]=1[CH3:51]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 18373917Acetonitrile--water (1/1)HCID 66784362N-Carbamoylmethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide

Product 1

HCID 86611480N-Aminomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide hydrochloride

Procedure

In a solution of 0.47 g of [bis(trifluoroacetoxy)iodo]benzene in 12 ml of acetonitrile-water (1:1), a solution of 0.47 g of N-carbamoylmethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide synthesized in Synthetic Example 31 was added with stirring at room temperature, and stirred at room temperature for 5 hours. After the completion of the reaction, 75 ml of water was added in the reaction mixture, 8 ml of concentrated hydrochloric acid was added, then washed with 100 ml of diethyl ether, and the organic phase was subjected to back extraction with 2N hydrochloric acid aqueous solution (20 ml×2). The aqueous phase was combined with the organic phase, water was distilled off, and the residual solid was washed with ethyl acetate to obtain 0.21 g of the aimed product as white crystal.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 5 hours
  3. additionwas added
  4. washwashed with 100 ml of diethyl ether
  5. extractionextraction with 2N hydrochloric acid aqueous solution (20 ml×2)
  6. distillationwas distilled off
  7. washthe residual solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-8ac4f4763d3140dc8ac35985fb299a26
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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