Methanol → HCID 19025399, compound
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[NH:12][C:13](=O)[CH3:14].CO>O1CCCC1>[CH2:13]([NH:12][C:3]1[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1])[CH3:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cold (0° C.), stirred solution of 6.3 g (0.029 mole) of N-(2,5-difluoro-4-nitrophenyl)acetamide in 100 ml of dry tetrahydrofuran was added dropwise 8.8 ml of a 10M boranedimethyl sulfide complex in tetrahydrofuran. The reaction mixture was heated until a gentle reflux was maintained with no external heating. When this reflux subsided, the mixture was reheated at reflux for three hours. The reaction mixture was cooled to 0° C., and methanol was added dropwise until no gas evolution was seen upon subsequent addition. This mixture was allowed to stand at room temperature for two days. The solvent was removed from the mixture by distillation under reduced pressure, leaving a residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride to yield 5.6 g of N-ethyl-2,5-difluoro-4-nitroaniline as a solid. The nmr spectrum was consistent with the proposed structure.
Workup
- temperatureThe reaction mixture was heated until
- temperaturea gentle reflux
- temperaturewas maintained with no external heating
- temperatureat reflux for three hours
- additionwas seen upon subsequent addition
- customThe solvent was removed from the mixture by distillation under reduced pressure
- customleaving a residue
- customThis residue was purified by column chromatography on silica gel
- washeluting with methylene chloride
Sources & evidence
- ORD record
- ord-c112a1a67c4f46e5bdf45ed2d6573583
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05108486
Reaction notes
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