Potassium Carbonate → HCID 73438561, compound

HRID 924616Notes

Reaction equation

HRID 924616 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:9]=1[C:10]([N:12]=[S:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:11].[Cl:24][C:25]1[C:26]([N:31]2[C:35]([C:36](Cl)=[O:37])=[CH:34][C:33]([C:39]([F:42])([F:41])[F:40])=[N:32]2)=[N:27][CH:28]=[CH:29][CH:30]=1>ClCCl>[Cl:24][C:25]1[C:26]([N:31]2[C:35]([C:36]([NH:7][C:8]3[C:9]([C:10](=[O:11])[N:12]=[S:13]([CH2:14][CH3:15])[CH2:16][CH3:17])=[CH:18][C:19]([Cl:23])=[CH:20][C:21]=3[Cl:22])=[O:37])=[CH:34][C:33]([C:39]([F:42])([F:40])[F:41])=[N:32]2)=[N:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 184469281-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl ChlorideHCID 86720247HCID 86720247, compound

Product 1

HCID 73438561HCID 73438561, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of potassium carbonate (7.06 g, 50 mmol, 1.50 equiv) and 2-amino-3,5-dichloro-N-(diethyl-λ4-sulfanylidene)benzamide (9.98 g, 34.05 mmol) in dichloromethane (50 mL) was added a solution of 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carbonyl chloride (13.8 g, 37.8 mmol, 1.10 equiv.) in dichloromethane (50 mL) at room temperature. After 3 h at this temperature, the solids were filtered off and water was added to the filtrate. The mixture was extracted with dichloromethane and dried over Na2SO4. After filtration, the filtrate was concentrated in vacuum and the resulting solids were crystallized from diethyl ether to yield the title compound (10.1 g, 52%).

Workup

  1. filtrationthe solids were filtered off
  2. additionwater was added to the filtrate
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuum
  7. customthe resulting solids were crystallized from diethyl ether

Sources & evidence

ORD record
ord-8676a5f16dbf4da8808ccc6afe7c8fc5
Source dataset
uspto-grants-2016_03
Patent number
US09282741B2

Reaction notes

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