Hydrochloric Acid → HCID 25157079, compound

HRID 1848322Notes

Reaction equation

HRID 1848322 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12](=O)[CH:13]=[C:14]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)[C:15]([F:18])([F:17])[F:16])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[OH-:28].[Na+].Cl.[NH2:31]O.Cl>O.CN1CCCC1=O.C1(C)C=CC=CC=1>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12]3[CH2:13][C:14]([C:19]4[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=4)([C:15]([F:18])([F:17])[F:16])[O:28][N:31]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 68612474HCID 68612474, compound

Product 1

HCID 25157079HCID 25157079, compoundYield 87.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

2.50 g of toluene and 1.50 g of N-methyl-2-pyrrolidone were added to 0.50 g (1.21 mmol) of 1-(6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one, and the mixture was cooled to 0° C. After adding in dropwise to this mixture the solution which was prepared by adding 0.49 g of water to 0.20 g (4.92 mmol) of sodium hydroxide, and then adding the solution in which 0.094 g (1.35 mmol) of hydroxylamine hydrochloride was dissolved into 0.20 g of water in dropwise, the mixture was stirred for 2 hours at 0° C. The aqueous solution which was prepared from 0.77 g (7.38 mmol) of 35% hydrochloric acid and 2.31 g of water was added in dropwise to the reaction solution, and the mixture was stirred for 1 hour. The reaction solution was cooled to room temperature, and separated by adding 20 ml of ethyl acetate and the ethyl acetate phase was washed twice with 10 ml of water. The solvent was distilled off under reduced pressure to obtain 0.45 g of 3-(6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (yield 87.3%).

Workup

  1. additionAfter adding in dropwise to this mixture the solution which
  2. customwas prepared
  3. additionwas added in dropwise to the reaction solution
  4. stirringthe mixture was stirred for 1 hour
  5. temperatureThe reaction solution was cooled to room temperature
  6. customseparated
  7. additionby adding 20 ml of ethyl acetate
  8. washthe ethyl acetate phase was washed twice with 10 ml of water
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d139968d32b14abeb5905b0449477ec8
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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