4-Fluoro-2-nitroaniline → 1-(4-Fluoro-2-nitrophenyl)-3-heptylurea

HRID 1901055Notes

Reaction equation

HRID 1901055 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]([N:19]=[C:20]=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:20]([NH:19][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:21])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 2

HCID 677694-Fluoro-2-nitroanilineHCID 138341n-Heptyl isocyanate

Product 1

HCID 233700951-(4-Fluoro-2-nitrophenyl)-3-heptylureaYield 66%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-fluoro-2-nitroaniline (1.56 g), heptyl isocyanate (1.41 g) and 4-dimethylaminopyridine (0.37 g) were stirred in toluene (5 ml) at 80°-90 C. for 5 hrs. This solution was diluted with ethyl acetate, washed with 1N hydrochloric acid, sodium hydrogen carbonate solution, water and saturated saline, dried over anhydrous MgSO4, and the solvent was distilled off. The resulted crystals were washed with hexane to give 1-(4-fluoro-2-nitrophenyl)-3-heptylurea (1.95 g, 66%).

Workup

  1. washwashed with 1N hydrochloric acid, sodium hydrogen carbonate solution, water and saturated saline
  2. dry with materialdried over anhydrous MgSO4
  3. distillationthe solvent was distilled off
  4. washThe resulted crystals were washed with hexane

Sources & evidence

ORD record
ord-6b67b22ba60e4bc386bee4bfdce6e342
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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