HCID 21419833, compound → HCID 68124691, compound

HRID 441275Notes

Reaction equation

HRID 441275 reaction equation
[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)[NH:9][C:10](=[O:18])[CH2:11][C:12](OC)([O:14][CH3:15])[CH3:13])(=[O:4])[CH2:2][CH3:3]>C1(C)C=CC=CC=1>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)[NH:9][C:10](=[O:18])/[CH:11]=[C:12](\[O:14][CH3:15])/[CH3:13])(=[O:4])[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 21419833HCID 21419833, compound

Product 1

HCID 68124691HCID 68124691, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 42.8 g of m-propionamido-3,3-dimethoxy-butyranilide in 500 ml of toluene was heated at 140° C. for 1 hour and was then let stand for 72 hours. The toluene was decanted and the residue was added to acetone. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8- 2 methylene chloride-acetone mixture to obtain 18 g of m-propionamido-3-methoxycrotonanilide melting at 155° C. Crystallization from ethyl acetate did not change the melting point.

Workup

  1. customThe toluene was decanted
  2. additionthe residue was added to acetone
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with an 8- 2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-265c25f6c9264b0fb072f900a38ee75b
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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