2,4-Difluoronitrobenzene → N-(1-(3,5-dichlorophenyl)ethyl)-5-fluoro-2-nitrobenzenamine

HRID 1910639Notes

Reaction equation

HRID 1910639 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([NH2:22])[CH3:21])[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([NH:22][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH3:21])[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 183341241-(3,5-Dichlorophenyl)ethanamine

Product 1

HCID 58707340N-(1-(3,5-dichlorophenyl)ethyl)-5-fluoro-2-nitrobenzenamineYield 11%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-difluoro-nitrobenzene (3.13 mmol), 1-(3,5-dichlorophenyl)ethanamine (3.13 mmol) and N,N-diisopropylethylamine (6.3 mmol) were stirred at 45° C. in dry acetonitrile (25 mL) for 16 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and purified by silica chromatography in 20% ethyl acetate in hexanes to collect the title compound (11% yield). 1H NMR (400 MHz, CDCl3): δ 9.23 (s, 1H), 7.87 (t, 1H), 7.28 (s, 1H), 7.19 (s, 2H), 6.41 (t, 1H), 6.11 (d, 1H), 4.51 (m, 1H), 1.62 (d, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. custompurified by silica chromatography in 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c16b0e523d4848bbaad2bf2e99631239
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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