Ammonia → HCID 22744069, compound

HRID 1978980Notes

Reaction equation

HRID 1978980 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([NH:9][NH2:10])=[O:8])=[CH:2]1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[C:19](O)=O.N>P(Cl)(Cl)(Cl)=O>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]2[O:8][C:19]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[C:12]([F:23])([F:11])[F:22])=[N:10][N:9]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 4686492-(Thiophen-3-yl)acetohydrazideHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-

Product 1

HCID 22744069HCID 22744069, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

880 mg of thiophene-3-acetic hydrazide were added to a solution of 960 mg of 4-trifluoromethylpyridine-3-carboxylic acid in 5 ml of phosphorus oxychloride, and the mixture was heated at reflux for 2 hours. The reaction mixture was subsequently added dropwise to ice-water, made neutral using concentrated ammonia solution and extracted with ethyl acetate. Drying (Na2SO4), concentration and chromatographic purification gave 624 mg of the desired product as a slightly brown oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. customDrying
  5. concentration(Na2SO4), concentration and chromatographic purification

Sources & evidence

ORD record
ord-8d900bd1f9b545ec893160e6cf45cb56
Source dataset
uspto-grants-2001_05
Patent number
US06239160B1

Reaction notes

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