Acetyl chloride → 3-(Acetylamino)-5-(octadecyloxy)nitrobenzene

HRID 1110278Notes

Reaction equation

HRID 1110278 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:29])[CH:7]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>C1COCC1>[C:37]([NH:29][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=1)(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 193889173-Nitro-5-(octadecyloxy)benzenamine

Product 1

HCID 193890243-(Acetylamino)-5-(octadecyloxy)nitrobenzeneYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.4 g (3.44 mmol) of 3-nitro-5-(octadecyloxy)benzenamine and 0.75 ml (5.4 mmol) of triethylamine in 85 ml of THF stirred in an ice bath was added 0.25 ml (3.44 mmol) of acetyl chloride. The ice bath was removed after 15 minutes and the reaction mixture was stirred at room temperature for 17 hours. Triethylamine (0.3 ml) and acetyl chloride (0.15 ml) were added and stirring was continued for 5 hours. The solvent was removed at reduced pressure and the residue was crystallized from ethyl acetate-hexane to give 1.3 g (84% yield, mp 103°-107°) of 3-(acetylamino)-5-(octadecyloxy)nitrobenzene. The structure was confirmed by nmr and mass spectra.

Workup

  1. customThe ice bath was removed after 15 minutes
  2. additionTriethylamine (0.3 ml) and acetyl chloride (0.15 ml) were added
  3. stirringstirring
  4. waitwas continued for 5 hours
  5. customThe solvent was removed at reduced pressure
  6. customthe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-311e5486adca4b3b9b36cc32ddd97fbe
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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