Chloroform → 3-[3-Chloro-4-(1-aminoethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

HRID 551318Notes

Reaction equation

HRID 551318 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])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[CH:25]([N:27]1C(=O)C2=CC=CC=C2C1=O)[CH3:26].C(Cl)(Cl)Cl>C(O)C.O.NN>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[CH:25]([NH2:27])[CH3:26]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 86631555N-[1-[2-chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl]ethyl]phthalimide

Product 1

HCID 866315563-[3-Chloro-4-(1-aminoethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazoleYield 84.3%

Reagents, catalysts & solvents 2

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

Procedure

In a solution of 0.40 g of N-[1-[2-chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl]ethyl]phthalimide in 10 mL of ethanol, 1.0 mL of 80% hydrazine monohydrate aqueous solution was added, and stirred under reflux with heating for 1 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 20 mL of chloroform was added therein and insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The procedure comprising adding 20 mL of chloroform in the residue, filtering off insoluble material and distilling off the solvent under reduced pressure was repeated twice to obtain 0.26 g of the aimed product as yellow resinous substance.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 1 hour
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. filtrationinsoluble substance was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionThe procedure comprising adding 20 mL of chloroform in the residue
  8. filtrationfiltering off insoluble material
  9. distillationdistilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-9cda99009d0d4520b2449de1566979ba
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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