Methanamine, N-methoxy-, hydrochloride (1:1) → 5-ethoxy-2-(4-fluorophenyl)-N-methoxy-N-methyl-2H-1,2,3-triazole-4-carboxamide
Reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C[Al](C)C.[CH2:10]([O:12][C:13]1[C:14]([C:25]([O:27]CC)=O)=[N:15][N:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[N:17]=1)[CH3:11]>>[CH2:10]([O:12][C:13]1[C:14]([C:25]([N:3]([O:4][CH3:5])[CH3:2])=[O:27])=[N:15][N:16]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[N:17]=1)[CH3:11]Participants
Conditions
- Temperature
- 0 °C
Procedure
To an oven-dried flask under a nitrogen atmosphere was added N,O-dimethylhydroxylamine hydrochloride (2.8 g, 28.6 mmol) to which a solution of trimethylaluminum (2.0 M in toluene, 14.3 mL, 28.6 mmol) was added at 0° C. and stirred for 30 min. Ethyl 5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step A, 4.0 g, 14.3 mmol) was added and the resulting solution was stirred at 23° C. for 4 h. The reaction mixture was cooled to 0° C. and carefully quenched by the dropwise addition of water (2 mL). Dichloromethane, (50 mL), sodium sulfate and water (3 mL) were added sequentially to the mixture which was then stirred for 20 min. at 23° C. The mixture was dried (Na2SO4 and MgSO4) and concentrated under reduced pressure to obtain the title compound (3.7 g) as an orange solid.
Workup
- additionwas added at 0° C.
- stirringthe resulting solution was stirred at 23° C. for 4 h
- customcarefully quenched by the dropwise addition of water (2 mL)
- additionDichloromethane, (50 mL), sodium sulfate and water (3 mL) were added sequentially to the mixture which
- stirringwas then stirred for 20 min. at 23° C
- dry with materialThe mixture was dried (Na2SO4 and MgSO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8c6f69353a0247be87b913c5791254fd
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302999B2
Reaction notes
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