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

HRID 1757834Notes

Reaction equation

HRID 1757834 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%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution d 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 (0.15ml ) 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 (0.15ml ) 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-2c27bcf633944561b4c0ffa182eb7724
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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