Nitrate → 3-Amino-5-pentafluorosulfanylbenzoic acid
Reaction equation
[F:1][S:2]([F:15])([F:14])([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[N+:16]([O-])([O-])=O.[H][H]>[Pd]>[NH2:16][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([S:2]([F:12])([F:13])([F:14])([F:15])[F:1])[CH:11]=1)[C:6]([OH:8])=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Proceeding from commercially available 3-(pentafluorosulfanyl)benzoic acid XIVa, reactions known to those skilled in the art were used first to nitrate it and then to reduce it to the amine with palladium on charcoal in the presence of hydrogen. The 3-amino-5-pentafluorosulfanylbenzoic acid XIIIa obtained was then dimethylated on the amine nitrogen under Eschweiler-Clark conditions, the carboxylic acid was converted with thionyl chloride to the acid chloride and the latter was reacted with O,N-dimethylhydroxylamine. The 3-dimethylamino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide XIIa thus obtained was converted with methylmagnesium bromide to the corresponding pentafluorosulfanyl derivatives of the formula Xa.
Sources & evidence
- ORD record
- ord-4393ab329f1c4e09a712f3d04aec917b
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466169B2
Reaction notes
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