1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl Chloride → HCID 73438561, compound

HRID 1410641Notes

Reaction equation

HRID 1410641 reaction equation
[NH2:1][C:2]1[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:3]=1[C:4]([N:6]=[S:7]([CH2:10][CH3:11])[CH2:8][CH3:9])=[O:5].[Cl:18][C:19]1[C:20]([N:25]2[C:29]([C:30](Cl)=[O:31])=[CH:28][C:27]([C:33]([F:36])([F:35])[F:34])=[N:26]2)=[N:21][CH:22]=[CH:23][CH:24]=1>N1C=CC=CC=1>[Cl:18][C:19]1[C:20]([N:25]2[C:29]([C:30]([NH:1][C:2]3[C:3]([C:4](=[O:5])[N:6]=[S:7]([CH2:8][CH3:9])[CH2:10][CH3:11])=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=3[Cl:16])=[O:31])=[CH:28][C:27]([C:33]([F:36])([F:34])[F:35])=[N:26]2)=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 184469281-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl ChlorideHCID 86720247HCID 86720247, compound

Product 1

HCID 73438561HCID 73438561, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 2-amino-3,5-dichloro-N-(diethyl-sulfanylidene)benzamide (8.82 g, 25.6 mmol) in pyridine (30 mL) was added N,N-dimethylamino pyridine (312 mg, 2.56 mmol, 10.0 mol %). At 90° C., a solution of 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carbonyl chloride (10.90 g, 29.12 mmol, 1.100 equiv.) in pyridine (50 mL) was added dropwise and the mixture was stirred for 1 h. The mixture was cooled and concentrated in vacuum. Water was added and the mixture was extracted with ethyl acetate. Combined organic layers were washed with water and brine, dried over sodium sulphate, filtered and concentrated in vacuum. Flash-chromatography on silica gel yielded the title compound (4.12 g, 28%).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuum
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washCombined organic layers were washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-4b957b3d69bb4841ac9237ed354eded0
Source dataset
uspto-grants-2014_12
Patent number
US08921567B2

Reaction notes

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