Water → 2-Cyclopentyl-N-(2,6-dimethyl-4-nitro-phenyl)-acetamide

HRID 1820118

Reaction equation

HRID 1820118 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[NH2:12].[CH:13]1([CH2:18][C:19](Cl)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1.O>C(#N)C>[CH:13]1([CH2:18][C:19]([NH:12][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][C:4]=2[CH3:11])=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 281592,6-Dimethyl-4-nitroanilineHCID 3485182Cyclopentylacetyl chloride

Product 1

HCID 687127672-Cyclopentyl-N-(2,6-dimethyl-4-nitro-phenyl)-acetamideYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

2,6-Dimethyl-4-nitro-phenylamine (0.98 g) and cyclopentylacetyl chloride (0.99 mL) were dissolved in acetonitrile (10 mL) and heated to 150° C. for 5 minutes in a sealed microwave process vial. Water (10 mL) was added to the reaction mixture, and the product was collected by filtration and washed with water (20 mL) and heptane (20 mL) to furnish 1.45 g (89% yield) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSO-d6): 1.24 (m, 2H), 1.54 (m, 2H), 1.63 (m, 2H), 1.79 (m, 2H), 2.25 (s, 6H), 2.27 (m, 1H), 2.36 (d, 2H), 7.98 (s, 2H), 9.56 (s, 1H).

Workup

  1. filtrationthe product was collected by filtration
  2. washwashed with water (20 mL) and heptane (20 mL)

Sources & evidence

ORD record
ord-4a398c3554bb4df49a1d0c78a5959536
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Linked notes

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