Water → HCID 73438578, compound

HRID 2166973Notes

Reaction equation

[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:3]=1[C:4]([N:6]=[S:7]([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])=[O:5].C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[C:28]([N:33]2[C:37]([C:38](Cl)=[O:39])=[CH:36][C:35]([C:41]([F:44])([F:43])[F:42])=[N:34]2)=[N:29][CH:30]=[CH:31][CH:32]=1.O>C1(C)C=CC=CC=1>[Cl:26][C:27]1[C:28]([N:33]2[C:37]([C:38]([NH:1][C:2]3[C:3]([C:4](=[O:5])[N:6]=[S:7]([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:9])[CH3:10])=[CH:14][C:15]([Cl:19])=[CH:16][C:17]=3[Cl:18])=[O:39])=[CH:36][C:35]([C:41]([F:44])([F:42])[F:43])=[N:34]2)=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the 2-amino-N-(bis-2-propyl-λ4-sulfanylidene)-3,5-dichloro-benzamide (26.2 g, 81.6 mmol) and potassium carbonate (12.4 g, 89.7 mmol) in toluene (80 mL) was added N,N-dimethylaminopyridine (0.50 g, 4.1 mmol). The reaction was then heated to 50° C. and 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride (32.3 g, 93.8 mmol) was added dropwise. After stirring for 2 h at this temperature water was added (50 mL) and the reaction stirred for a further 15 min, then cooled to 0° C. and stirred for a further 30 min. The resulting solid was filtered and washed with water and toluene (minimal) to afford the title compound (32.0 g, 66%).

Workup

additionwas added (50 mL)
temperaturecooled to 0° C.
stirringstirred for a further 30 min
filtrationThe resulting solid was filtered
washwashed with water and toluene (minimal)

Sources & evidence

ORD record: ord-18a55ae848bc487687a28f9de4eff18d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09044016B2

Reaction notes

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