Sulfuric Acid → N(m-propionamidophenyl)-2,2-dimethylsuccinimide

HRID 1982078Notes

Reaction equation

HRID 1982078 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[C:9]([N:13]2[C:17](=[O:18])[CH2:16][C:15]([CH3:20])([CH3:19])[C:14]2=[O:21])[CH:10]=[CH:11][CH:12]=1>C(OC(=O)CC)(=O)CC.O>[C:17]([NH:6][C:7]1[CH:8]=[C:9]([N:13]2[C:17](=[O:18])[CH2:16][C:15]([CH3:19])([CH3:20])[C:14]2=[O:21])[CH:10]=[CH:11][CH:12]=1)(=[O:18])[CH2:16][CH3:15]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13189216N-m-AMINOPHENYL-2,2-DIMETHYLSUCCINIMIDE

Product 1

HCID 23317140N(m-propionamidophenyl)-2,2-dimethylsuccinimide

Reagents, catalysts & solvents 2

HCID 31263Propionic anhydrideCatalystHCID 962WaterSolvent

Procedure

Five and one half g. of propionic anhydride containing one drop of concentrated sulfuric acid was mixed at ambient temperature with 8.7 g. of N-m-aminophenyl-2,2-dimethylsuccinimide in a small beaker. The mixture became very hot and on cooling was poured into water and extracted with methylene chloride, which was dried and stripped under vacuum yielding 9.5 g. of a glassy product. The product was identified as the title compound by analysis of infrared spectra.

Workup

  1. temperatureon cooling
  2. extractionextracted with methylene chloride, which
  3. customwas dried
  4. customyielding 9.5 g

Sources & evidence

ORD record
ord-2cf23612caed45fb91d44532bc23b0cb
Source dataset
uspto-grants-1986_06
Patent number
US04595408

Reaction notes

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