Acetic Acid → Acetanilide

HRID 257238Notes

Reaction equation

HRID 257238 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](O)(=O)C.C([Sn](Cl)(Cl)CCCC)CCC>C(Cl)Cl>[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])[CH3:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7672Phenyl isocyanate2×HCID 12688Dibutyltin dichloride2×

Product 1

HCID 904AcetanilideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.19 g phenyl isocyanate was reacted with 0.6 g acetic acid in a 1:1 molar ratio in the presence of dibutyltin dichloride in methylene chloride (20 parts). The molar ratio of dibutyltin dichloride to phenyl isocyanate was 1:100. The reaction, product isolation and analysis were conducted as in Example 1. A 97.0% yield of acetanilide was obtained (1.20 g).

Workup

  1. customThe reaction, product isolation and analysis

Sources & evidence

ORD record
ord-ac856e70cdc746d791a50962fe422218
Source dataset
uspto-grants-1993_11
Patent number
US05260483

Reaction notes

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