Acetic Anhydride → HCID 59410103, compound

HRID 2404852Notes

Reaction equation

HRID 2404852 reaction equation
[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=2[N+:14]([O-:16])=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(Cl)Cl>[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:24](=[O:26])[CH3:25])=[CH:9][C:8]=2[N+:14]([O-:16])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22279241HCID 22279241, compound

Product 1

HCID 59410103HCID 59410103, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyclohexyl-3-nitro-aniline (1.54 g, 6.99 mmol) in DCM (15 mL) was added Et3N (1.9 mL, 13.63 mmol), followed by the addition of acetic anhydride (3.3 mL, 34.98 mmol). The reaction mixture was stirred at room temperature for 2 h, quenched with water, the layers separated and the organic layer was washed with 0.1N HCl, followed by washing with H2O. The organic layer was dried over MgSO4, filtered and concentrated to obtain N-(4-cyclohexyl-3-nitrophenyl)acetamide (1.7 g, 93%). 1H NMR (400 MHz, CDCl3) δ 7.91 (d, J=2.2 Hz, 1H), 7.69 (dd, J=8.6, 2.2 Hz, 1H), 7.52 (s, 1H), 7.40 (d, J=8.6 Hz, 1H), 3.01-2.87 (m, 1H), 2.22 (s, 3H), 1.95-1.78 (m, 5H), 1.42 (t, J=10.4 Hz, 4H), 1.32-1.21 (m, 1H).

Workup

  1. customquenched with water
  2. customthe layers separated
  3. washthe organic layer was washed with 0.1N HCl
  4. washby washing with H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-45a4d2bff2f84bc9ae197e7285118580
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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