4-Dodecylaniline → N-(4-dodecylphenyl)acetamide

HRID 231636

Reaction equation

HRID 231636 reaction equation
[CH2:1]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:20](OC(=O)C)(=[O:22])[CH3:21]>C1(C)C=CC=CC=1>[C:20]([NH:17][C:16]1[CH:15]=[CH:14][C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:19][CH:18]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 77014-DodecylanilineHCID 7918Acetic Anhydride2×

Product 1

HCID 299609N-(4-dodecylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

In a 1-liter flask fitted with a stirrer and reflux condenser is added 137.5 grams (0.525 mole) of p-n-dodecylaniline, dissolved in 138 ml of toluene. To this is added over a 15-minute period 57.5 ml of acetic anhydride. The temperature rises from 40° to 80° C. After all the acetic anhydride is added, the reaction mixture is stirred at 40° C. for 3 hours. The reaction mixture is then cooled to yield the crude product which is recrystallized from 800 ml of methanol to give 151.1 grams of the above-named material as a solid melting at 100°-102° C.

Workup

  1. customIn a 1-liter flask fitted with a stirrer
  2. temperaturereflux condenser
  3. customrises from 40° to 80° C
  4. temperatureThe reaction mixture is then cooled
  5. customto yield the crude product which
  6. customis recrystallized from 800 ml of methanol

Sources & evidence

ORD record
ord-95121b24eac24c9d8a87216f41a1c7d6
Source dataset
uspto-grants-1989_07
Patent number
US04847367

Linked notes

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