Dimethyl Sulfoxide → 2-Pyridinamine, 3-chloro-N-(3-ethoxy-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-
Reaction equation
[CH2:1]([OH:3])[CH3:2].[H-].[Na+].[Cl:6][C:7]1[C:8]([NH:17][C:18]2[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([C:27]([F:30])([F:29])[F:28])=[C:20](Cl)[C:19]=2[N+:32]([O-:34])=O)=[N:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1.CS(C)=O.[OH2:39]>>[Cl:6][C:7]1[C:8]([NH:17][C:18]2[C:19]([N+:32]([O-:34])=[O:39])=[CH:20][C:21]([C:27]([F:30])([F:28])[F:29])=[C:22]([O:3][CH2:1][CH3:2])[C:23]=2[N+:24]([O-:26])=[O:25])=[N:9][CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1Participants
6
Procedure
In 30 ml. of ethanol, 1.5 g. of sodium hydride was added with stirring and a solution of 7.0 g. of N-(3-chloro-5-trifluoromethyl-2-pyridyl)-2,6-dinitro-3-chloro-4-trifluoromethylaniline (obtained in Preparation 4) in 50 ml. of dimethylsulfoxide was added dropwise to react them at room temperature for 3 hours. The reaction mixture was poured into water and the product was extracted with methylene chloride. The extracted layer was washed with water and dehydrated and the solvent was distilled, the product was separated by a silica gel column with an eluent of a mixture of n-hexane and ethyl acetate (4:1) and the solvent was distilled off to obtain 4.0 g. of the object compound having the melting point of 106° to 108° C.
Workup
- customto react them at room temperature for 3 hours
- extractionthe product was extracted with methylene chloride
- washThe extracted layer was washed with water
- distillationthe solvent was distilled
- customthe product was separated by a silica gel column with an eluent of a mixture of n-hexane and ethyl acetate (4:1)
- distillationthe solvent was distilled off
- customto obtain 4.0 g
Sources & evidence
- ORD record
- ord-203d99bc989f40ebbbb4e923df10f59d
- Source dataset
- uspto-grants-1982_05
- Patent number
- US04331670
Reaction notes
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