p-Toluidine → 4-Methylacetanilide

HRID 1739618Notes

Reaction equation

HRID 1739618 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:9](=[O:11])[CH3:10])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 7813p-ToluidineHCID 7918Acetic Anhydride

Product 1

HCID 76844-MethylacetanilideYield 97%

Procedure

Into three neck round bottom flask (5 L) equipped with a mechanical stirrer, a condenser, and an addition funnel, were added p-toluidine (995 g, 9.3 mol) and hexanes (1.6 L). Acetic anhydride (960 mL, 10.2 mol) was added dropwise for 2 h enough to reflux, then refluxed for 1 h and cooled to room temperature to give a brown solid. This was collected by suction filtration, transferred into a beaker, and washed with water (2 L) for 30 min. The filtration and washing procedures were repeated. The wet white crystals were air dried for 7 days to provide N-(4-methylphenyl)acetamide (1,343 g, 97% yield). Melting point: 150-152° C. (lit. 153° C., Merck index. 11, 67;).

Workup

  1. customInto three neck round bottom flask (5 L) equipped with a mechanical stirrer, a condenser, and an addition funnel
  2. temperatureto reflux
  3. temperaturerefluxed for 1 h
  4. customto give a brown solid
  5. filtrationThis was collected by suction filtration
  6. washwashed with water (2 L) for 30 min
  7. filtrationThe filtration
  8. washwashing procedures
  9. customdried for 7 days

Sources & evidence

ORD record
ord-d5301d352c4d4042b1bfe9deac235da7
Source dataset
uspto-grants-1999_10
Patent number
US05968674

Reaction notes

Loading…