Sodium Iodide → HCID 67407516, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[NH2:13].Cl[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Cl.[I-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[NH2:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 165 °C
Procedure
2-Chloro-6-trifluoromethyl-benzene-1,4-diamine (2.9 g), bis-(2-chloroethyl)ether (1.7 mL) and sodium iodide (516 mg) were mixed in acetonitrile (45 mL) and heated to 165° C. for 1 hour in a sealed microwave process vessel. The crude mixture was concentrated in vacuo, redissolved in ethyl acetate (100 mL) and washed with water (2×100 mL) and brine (1×100 mL). The organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 940 mg (24%) of the title compound as a black oil. 1H NMR (500 MHz, CDCl3): 3.02 (m, 4H), 3.84 (m, 4H), 4.30 (b, 2H), 6.97 (d, 1H), 7.06 (d, 1H).
Workup
- concentrationThe crude mixture was concentrated in vacuo
- dissolutionredissolved in ethyl acetate (100 mL)
- washwashed with water (2×100 mL) and brine (1×100 mL)
- dry with materialThe organic phase was dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-bb8cb8cbcc9d49f2b2bd7a8dd9118a36
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07501414B2
Reaction notes
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