Ammonia → 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrazole-3-carboxamide

HRID 2099037Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=C(C(O)=O)[C:3]=1[S:22][C:23]([F:26])([F:25])[F:24].[NH3:27].[O:28]1[CH2:33][CH2:32]OCC1>O>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:32]([C:33]([NH2:27])=[O:28])[C:3]=1[S:22][C:23]([F:26])([F:25])[F:24]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid (1.00 g, 2.27 mmol) and 1,1-dicarbonylimidazole (0.45 g, 2.72 mmol) in dioxane was heated to 50° C. for 2 hours. An aqueous solution of ammonia (33%, 80 ml) was then added and stirring continued at 50° C. for 4 hours. The cooled mixture was diluted with water and extracted with ethyl acetate/heptane (1:1). The combined organic phase was washed with aqueous potassium hydrogensulfate (5%), dried over magnesium sulfate and evaporated to give the title compound (0.980 g, yield 98%) as a white foam, 1H NMR (CDCl3): 4.36 (bs, 2H, NH2), 5.60 and 6.69 (bs, 2H, C(O)NH2), and 7.82 (s, 2H, Ar—H).

Workup

extractionextracted with ethyl acetate/heptane (1:1)
washThe combined organic phase was washed with aqueous potassium hydrogensulfate (5%)
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-0a05a9f7d6bb4a008ed49a3fc590fad7
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569516B2

Reaction notes

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