Sodium Carbonate → N-{4-[(cyclohexylmethyl)amino]-3-nitrophenyl}acetamide

HRID 472938Notes

Reaction equation

HRID 472938 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>CCO.O>[CH:1]1([CH2:7][NH:8][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][C:11]=2[N+:20]([O-:22])=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 67694Acetamide, N-(4-fluoro-3-nitrophenyl)-HCID 76688Cyclohexanemethylamine

Product 1

HCID 57591007N-{4-[(cyclohexylmethyl)amino]-3-nitrophenyl}acetamideYield 113.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Cyclohexylmethylamine (2.86 mL, 2.49 g, 22.0 mmol) was added to a mixture of N-(4-fluoro-3-nitrophenyl)acetamide (3.96 g, 20.0 mmol) and sodium carbonate (4.66 g, 44 mmol) in EtOH (50 mL) at room temperature. The reaction mixture was heated for 48 h at 60° C., and diluted with H2O (800 mL). The orange solid was precipitated out and collected to give the desired product (6.60 g, 100%). MS (ESI) (M+H)+: 292.32.

Workup

  1. customThe orange solid was precipitated out and
  2. customcollected

Sources & evidence

ORD record
ord-cdf843fb51d3441d98b46047af1ea159
Source dataset
uspto-grants-2014_01
Patent number
US08633235B2

Reaction notes

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