Pyrazole → N,N-dimethyl-1H-pyrazole-1-sulfonamide
Reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][N:4](C2C=NC=CC=2)[N:3]=1.BrC1C=NC=CC=1.Cl[C:21]1[CH:25]=[CH:24][NH:23][N:22]=1.N1C=CC=N1.[CH3:31][N:32]([CH3:37])[S:33](Cl)(=[O:35])=[O:34].[H-].[Na+]>>[Cl:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[CH3:31][N:32]([CH3:37])[S:33]([N:23]1[CH:24]=[CH:25][CH:21]=[N:22]1)(=[O:35])=[O:34]Participants
Procedure
US 20130288893(A1) describes, inter alia, certain (3-halo-1-(pyridin-3-yl)-1H-pyrazol-4-yl)amides and carbamates and their use as pesticides. The route to prepare such compounds involved the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine by the direct coupling of 3-bromopyridine with 3-chloropyrazole. The 3-chloropyrazole was prepared by a) treating 1H-pyrazole with 2 dimethylsulfamoyl chloride and sodium hydride to provide N,N-dimethyl-1H-pyrazole-1-sulfonamide, b) treating the N,N-dimethyl-1H-pyrazole-1-sulfonamide with perchloroethane and n-butyl lithium to provide 3-chloro-N,N-dimethyl-1H-pyrazole-1-sulfonamide, and c) removing the N,N-dimethylsulfonamide from 3-chloro-N,N-dimethyl-1H-pyrazole-1-sulfonamide with trifluoroacetic acid to give the 3-chloropyrazole.
Workup
- customThe route to prepare such compounds
Sources & evidence
- ORD record
- ord-2a03cfb05023492ca6503b714575bfc6
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09024031B1
Reaction notes
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