Chloroform → 3-(4-Aminomethyl-3-chlorophenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

HRID 1880236Notes

Reaction equation

HRID 1880236 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[CH2:26][N:27]1C(=O)C2=CC=CC=C2C1=O.C(Cl)(Cl)Cl>C(O)C.O.NN>[NH2:27][CH2:26][C:3]1[CH:4]=[CH:5][C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 86761690N-[[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methyl]phthalimide

Product 1

HCID 446282993-(4-Aminomethyl-3-chlorophenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

To a solution of 3.0 g of N-[[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methyl]phthalimide in 70 mL of ethanol, 1.0 mL of 80% hydrazine monohydrate was added and the resultant mixture was stirred while heating the mixture to reflux for 1 hour. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and 100 mL of chloroform was added to the reaction mixture to filter off an insoluble substance, followed by distilling off the solvent under reduced pressure. To the resultant residue, 50 mL of chloroform was added to dissolve the residue and to filter off the resultant insoluble substance. The filtrate was washed with water (50 mL×1) and then dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order and the solvent was distilled off under reduced pressure to obtain 2.55 g of the objective substance as a yellow resinoid.

Workup

  1. temperaturewhile heating the mixture
  2. temperatureto reflux for 1 hour
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. filtrationto filter off an insoluble substance
  6. distillationby distilling off the solvent under reduced pressure
  7. additionTo the resultant residue, 50 mL of chloroform was added
  8. dissolutionto dissolve the residue
  9. filtrationto filter off the resultant insoluble substance
  10. washThe filtrate was washed with water (50 mL×1)
  11. dry with materialdried over saturated saline and anhydrous magnesium sulfate in this order
  12. distillationthe solvent was distilled off under reduced pressure
  13. customto obtain 2.55 g of the objective substance as a yellow resinoid

Sources & evidence

ORD record
ord-4e17af1e6c834e0eb8b2b5da0a296f1a
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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