Acetyl chloride → N-Methyl-N-(4-nitrophenyl)acetamide

HRID 2092382Notes

Reaction equation

HRID 2092382 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.CCN(CC)CC.[C:19](Cl)(=[O:21])[CH3:20].CCOC(C)=O>C1COCC1.CN(C1C=CN=CC=1)C>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[C:19](=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 7483N-Methyl-4-nitroanilineHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 67143N-Methyl-N-(4-nitrophenyl)acetamideYield 108.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-4-nitroaniline (200 mg, 1.31 mmol) in THF (5 ml) were successively added Et3N (0.364 ml, 2.63 mmol), acetyl chloride (0.14 ml, 1.97 mmol) and DMAP (8.0 mg, 0.066 mmol) at RT. The reaction mixture was stirred at RT for 2 h then diluted into AcOEt and washed with water. The organic layer was dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (275 mg) as a brownish solid, which was used in the next step without further purification. HPLC: AtRet=1.17 min; LC-MS: m/z 195.4 [M+H]+; 1H NMR (400 MHz, CDCl3): 2.05 (br. s., 3H), 3.37 (s, 3H), 7.36-7.46 (m, 2H), 8.27-8.36 (m, 2H).

Workup

  1. customat RT
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-feb19d8e453d4f198e3fff8af125ff34
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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