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

HRID 1470777Notes

Reaction equation

HRID 1470777 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-λ4-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-43474cc0fd384af0b4d2574500c8f5a7
Source dataset
uspto-grants-2015_04
Patent number
US09006485B2

Reaction notes

Loading…