3-Fluoro-4-nitroaniline → Cyclohexyl-n-(3-fluoro-4-nitrophenyl)carboxamide

HRID 722412

Reaction equation

HRID 722412 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].[CH:12]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl.C1COCC1.N1C=CC=CC=1.C(Cl)Cl>[CH:12]1([C:18]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:2]([F:1])[CH:3]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 2

HCID 754013-Fluoro-4-nitroanilineHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 58742600Cyclohexyl-n-(3-fluoro-4-nitrophenyl)carboxamideYield 80.7%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

3-Fluoro-4-Nitroaniline (1 mmol, 0.15 g) was dissolved in a 3:1 mixture of CH2Cl2/THF (4 mL) and pyridine (0.2 mL) was added to the mixture, which was cooled in an ice-water bath under nitrogen. Cyclohexanecarbonylchloride (1.1 mmol, 0.162 g) was dissolved in CH2Cl2 (1 mL) and added dropwise to the above solution at 4° C. and stirred at room temperature for 3 h. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with 1N HCl, 10% NaHCO3, brine and water, dried over Na2SO4 and the solvent evaporated to afford cyclohexyl-N-(3-fluoro-4-nitrophenyl)carboxamide (0.215 g) of product (Yield: 81%).

Workup

  1. additionwas added to the mixture, which
  2. temperaturewas cooled in an ice-water bath under nitrogen
  3. additionadded dropwise to the above solution at 4° C.
  4. washwashed with 1N HCl, 10% NaHCO3, brine and water
  5. dry with materialdried over Na2SO4
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-742fac2e64c547abbb39b88fb01a7247
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Linked notes

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