p-Toluenesulfonic acid → N,N-dimethyl-2-hydroxyimino-3-(4-methoxyphenylimino)butyramide

HRID 971895Notes

Reaction equation

HRID 971895 reaction equation
[CH3:1][N:2]([CH3:11])[C:3](=[O:10])[C:4](=[N:8][OH:9])[C:5]([CH3:7])=O.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:11])[C:3](=[O:10])[C:4](=[N:8][OH:9])[C:5](=[N:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1)[CH3:7]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7732P-AnisidineHCID 178468379HCID 178468379, compound

Product 1

HCID 136409746N,N-dimethyl-2-hydroxyimino-3-(4-methoxyphenylimino)butyramide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

a mixture of 142 parts of N,N-dimethyl-2-hydroxyiminoacetoacetamide (a compound of Formula III), 1200 parts of toluene, 123 parts of p-anisidine and 1 part of p-toluenesulfonic acid was refluxed overnight in a flask fitted with a Dean-Stark distilling trap and water condenser. Eighteen parts of water were removed in this manner. On cooling, a heavy slurry of solid product precipitated. This was filtered and washed with butyl chloride thereby providing a product which melted at 201.5°-203° C. Recrystallization from acetonitrile gave 151 parts of N,N-dimethyl-2-hydroxyimino-3-(4-methoxyphenylimino)butyramide (a compound of Formula II) as a yellow solid, m.p. 204°-205.5° C.

Workup

  1. temperaturewas refluxed overnight in a flask
  2. customfitted with a Dean-Stark
  3. distillationdistilling trap and water condenser
  4. customEighteen parts of water were removed in this manner
  5. temperatureOn cooling
  6. customa heavy slurry of solid product precipitated
  7. filtrationThis was filtered
  8. washwashed with butyl chloride
  9. customthereby providing a product which melted at 201.5°-203° C
  10. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-834c357542014030aae83fe1fd769f93
Source dataset
uspto-grants-1979_07
Patent number
US04161591

Reaction notes

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