Aniline → Acetanilide

HRID 1577621Notes

Reaction equation

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

Participants

Reactant 2

HCID 6115Aniline

HCID 6367Acetyl chloride

Product 1

HCID 904AcetanilideYield 81%

Procedure

Acetanilide is prepared by the method of Example 5 using 5.0 mls (0.055 mole) of aniline, 7.5 grams of Type 3A molecular sieves, and 4.58 mls (0.064 mole) of acetyl chloride. The crude product is recrystallized from toluene to obtain 5.87 grams (81% of theoretical) of pure acetanilide, m.p. 112°-114° C. (literature m.p. 114° C.).

Workup

customThe crude product is recrystallized from toluene

Sources & evidence

ORD record: ord-2109590d080942d5a0d755559be36b56
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04288592

Reaction notes

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