p-Toluenesulfonic acid → 2,5-Dimethyl-3-furancarboxanilide

HRID 597258

Reaction equation

HRID 597258 reaction equation
C(O[CH:5]([CH3:8])[CH:6]=O)(=O)C.[C:9]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:13][C:11]1[O:12][C:5]([CH3:8])=[CH:6][C:10]=1[C:9]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7592AcetoacetanilideHCID 907282-(Acetyloxy)propanal

Product 1

HCID 342812,5-Dimethyl-3-furancarboxanilide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 24 parts of α-acetoxypropionaldehyde, 35.4 parts of acetoacetanilide and 2 parts of p-toluenesulfonic acid in 100 parts of benzene is kept for 3 hours at 40° C and then boiled under reflux for 1 hour. Adopting the isolation procedure described in Example 1 there is obtained 41.8 parts of 2,5-dimethylfuran-3-carboxanilide having a melting point of 92° to 93° C.

Workup

  1. temperatureunder reflux for 1 hour

Sources & evidence

ORD record
ord-5f59a1c4dbd54bfb931d73bada34606e
Source dataset
uspto-grants-1977_03
Patent number
US04013684

Linked notes

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