Pyridine → HCID 68702137, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[C:12]=1[O:13][CH3:14])[C:6](Cl)=NC.[N:18]1[NH:19]N=[N:21][C:22]=1[C:23]1[C:24]([C:29]([F:32])([F:31])[F:30])=[N:25][CH:26]=[CH:27][CH:28]=1.N1C=CC=C[CH:34]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[N:21]([CH3:34])[C:22]([C:23]3[C:24]([C:29]([F:32])([F:31])[F:30])=[N:25][CH:26]=[CH:27][CH:28]=3)=[N:18][N:19]=2)[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[C:12]=1[O:13][CH3:14]Participants
4
Conditions
- Temperature
- 82.5 °C
Procedure
3,4-Dimethoxy-N-methyl-5-nitro-benzimidoyl chloride (0.28 g, 1.08 mmol) was added to a stirred solution of 3-(2H-tetrazol-5-yl)-2-(trifluoromethyl)pyridine (0.215 g, 1 mmol) in dry pyridine (3 mL), preheated to 50° C. The resulting mixture was cautiously heated to 75-90° C. and maintained at this temperature until nitrogen evolution ceased. The mixture was then poured onto water (30 mL) and extracted with dichloromethane (25 mL). The organic phase was separated, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The resulting residue was purified by chromatography to afford 3-(5-(3,4-dimethoxy-5-nitrophenyl)-4-methyl-4H-1,2,4-triazol-3-yl)-2-(trifluoromethyl)pyridine, 0.241 g (59%).
Workup
- custompreheated to 50° C
- temperaturemaintained at this temperature until nitrogen evolution
- additionThe mixture was then poured onto water (30 mL)
- extractionextracted with dichloromethane (25 mL)
- customThe organic phase was separated
- dry with materialdried over anhydrous magnesium sulphate
- filtrationfiltered
- customevaporated to dryness
- customThe resulting residue was purified by chromatography
Sources & evidence
- ORD record
- ord-993bd659aac04887bd24f303e3591b9f
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446012B2
Reaction notes
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