Sodium Cyanide → Amino[2-chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl]acetonitrile

HRID 551319Notes

Reaction equation

[C-:1]#[N:2].[Na+].[Cl-].[NH4+:5].[Cl:6][C:7]1[CH:14]=[C:13]([C:15]2[CH2:19][C:18]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)[CH:12]=[CH:11][C:8]=1[CH:9]=O>O.N.CO.C(OCC)(=O)C>[NH2:5][CH:9]([C:8]1[CH:11]=[CH:12][C:13]([C:15]2[CH2:19][C:18]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)=[CH:14][C:7]=1[Cl:6])[C:1]#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

In a solution of 0.18 g of sodium cyanide and 0.29 g of ammonium chloride in 5 mL of 28% ammonia water, a solution of 1.0 g of 2-chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]benzaldehyde synthesized in Step 6 of Synthetic Example 6 in 30 mL of methanol was added, and stirred at 60° C. for 2 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, diluted with 60 mL of ethyl acetate, washed with water (30 mL×2), and the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and the solvent was distilled off under reduced pressure to obtain 1.10 g of the aimed product as pale brown resinous substance.

Workup

customAfter the completion of the reaction
waitthe reaction mixture was left
temperaturecooled to room temperature
washwashed with water (30 mL×2)
dry with materialdried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-065aa0ee4615451e989fe2ce0937779c
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947715B2

Reaction notes

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