Hydrochloric Acid → 1-[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl]-2-cyanophenyl]-1H-1,2,4-triazole

HRID 1848323Notes

Reaction equation

HRID 1848323 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:26]([F:29])([F:28])[F:27])=[CH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([N:21]3[CH:25]=[N:24][CH:23]=[N:22]3)=[C:17]([CH:20]=2)[C:18]#[N:19])=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-:30].[Na+].Cl.[NH2:33]O.Cl>C1(C)C=CC=CC=1.O.CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:26]([F:29])([F:28])[F:27])[O:30][N:33]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([N:21]4[CH:25]=[N:24][CH:23]=[N:22]4)=[C:17]([CH:20]=3)[C:18]#[N:19])[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 673771115-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-(1H-1,2,4-triazol-1-yl)benzonitrile

Product 1

HCID 236422431-[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl]-2-cyanophenyl]-1H-1,2,4-triazoleYield 94.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 1140TolueneSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

1.52 g of toluene and 0.91 g of N-methyl-2-pyrrolidone were added to 0.30 g (0.96 mmol) of 5-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-(1H-1,2,4-triazol-1-yl)benzonitrile, and the mixture was cooled to 0° C. After adding in dropwise to this mixture the aqueous solution which was prepared by adding 0.28 g of water to 0.11 g (2.77 mmol) of sodium hydroxide, and then adding the solution in which 0.053 g (0.76 mmol) of hydroxylamine hydrochloride was dissolved into 0.11 g of water in dropwise, the mixture was stirred for 2 hours at 0° C. The aqueous solution which was prepared from 0.43 g (4.16 mmol) of 35% hydrochloric acid and 1.30 g of water was added in dropwise to the reaction solution, and the mixture was stirred for 1 hour. 5 ml of toluene was added and separation operation was performed. The toluene phase was washed twice with 3 ml of water. The solvent was distilled off under reduced pressure to obtain 0.30 g of 5-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl)-2-(1H-1,2,4-triazol-1-yl)benzonitrile (yield 94.5%).

Workup

  1. additionAfter adding in dropwise to this mixture the aqueous solution which
  2. customwas prepared
  3. additionwas added in dropwise to the reaction solution
  4. stirringthe mixture was stirred for 1 hour
  5. customseparation operation
  6. washThe toluene phase was washed twice with 3 ml of water
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fc794b3948884603a01ae788569d91da
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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