Reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12](F)[CH:11]=[C:10]([F:18])[CH:9]=1)[CH3:2].C(N(CC)CC)C.[CH2:28]([NH2:32])[CH2:29][CH2:30][CH3:31]>CN(C=O)C>[CH2:28]([NH:32][C:12]1[CH:11]=[C:10]([F:18])[CH:9]=[C:8]([O:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:19][CH3:20])[CH2:1][CH3:2])[C:13]=1[N+:14]([O-:16])=[O:15])[CH2:29][CH2:30][CH3:31]Participants
5
Procedure
To a stirred solution of 6-(3-diethylaminopropoxy)-2,4-difluoronitrobenzene (11 mmol) and triethylamine (22 mmol) in DMF (20 mL), a solution of n-butylamine (11 mmol) in DMF (8 mL) was added dropwise at rt, and the mixture was stirred at rt for 10 h. The reaction was quenched by cold H2O (50 mL), and the resulting mixture was extracted with EtOAc (3×100 mL). The combined EtOAc extracts were washed with brine (3×50 mL) and dried (anhydrous Na2SO4). The solvent was removed in vacuo to afford the desired 2-n-butylamino-6-(3-diethylaminopropoxy)-4-fluoronitrobenzene which was used for further transformation.
Workup
- customThe reaction was quenched by cold H2O (50 mL)
- extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
- washThe combined EtOAc extracts were washed with brine (3×50 mL)
- dry with materialdried (anhydrous Na2SO4)
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-da35513542f84da8825139e72ef6d024
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737285B2
Linked notes
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