Acetic Anhydride → N-(3,5-Dimethylphenyl)acetamide

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:12])[CH3:11])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 79493,5-Dimethylaniline

Product 1

HCID 74903N-(3,5-Dimethylphenyl)acetamideYield 93.9%

Conditions

Temperature: 100 °C

Procedure

A mixture of the 3,5-dimethylaniline (12.1 g, 100.0 mmol) and acetic anhydride (12.1 g, 118.6 mmol) was stirred at 100° C. for 1 h. The crude product was then recrystallized from methanol to provide N-(3,5-dimethylphenyl)acetamide (15.3 g, 93.9%) as a white flake; m.p. 140-142° C. (Lit. 139.6-140.2° C.5.

Workup

customThe crude product was then recrystallized from methanol

Sources & evidence

ORD record: ord-adaba23462ed475fbd9501f5d7e13947
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422275B2

Reaction notes

Loading…