Iodopentafluoroethane → N,N,N'-Trimethyl-N'-(2-nitro-4-pentafluoroethyl-phenyl)-propane-1,3-diamine
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:15])[CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[F:19][C:20](I)([F:25])[C:21]([F:24])([F:23])[F:22]>[Cu].CS(C)=O>[CH3:13][N:12]([CH3:14])[CH2:11][CH2:10][CH2:9][N:8]([CH3:15])[C:5]1[CH:6]=[CH:7][C:2]([C:20]([F:25])([F:19])[C:21]([F:24])([F:23])[F:22])=[CH:3][C:4]=1[N+:16]([O-:18])=[O:17]Participants
5
Conditions
- Temperature
- 120 °C
Procedure
To a pressure vessel was added N-(4-Bromo-2-nitro-phenyl)-N, N′,N′-trimethyl-propane-1,3-diamine (Step 1, 5.0 g, 15.8 mmol), copper powder (10.0 g, 158 mmol), and 20 mL DMSO. Pentafluoroethyl iodide (7.8 g, 31.6 mmol) was bubbled in and the vessel sealed. The mixture was then heated to 120° C. and vigorously stirred for 22 h. The reaction was cooled to 0° C. and filtered through a Buchner funnel, rinsing with EtOAc. The filtrate was then washed once with saturated aqueous NaHCO3, twice with water, once with brine, and then dried over Mg2SO4. The crude mixture was then purified by silica gel chromatography using a 10% MeOH/CH2Cl2 gradient to yield the title compound as a brown oil. MS (M+H)+=356; Calc'd 355.30 for C14H18F5N3O2.
Workup
- customsealed
- temperatureThe reaction was cooled to 0° C.
- filtrationfiltered through a Buchner funnel
- washrinsing with EtOAc
- washThe filtrate was then washed once with saturated aqueous NaHCO3, twice with water, once with brine
- dry with materialdried over Mg2SO4
- customThe crude mixture was then purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-ec72e130dc85485cbf982389daa8f24f
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07880000B2
Reaction notes
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