p-Toluenesulfonic acid → Acrylamidomethyl 2-oxopyrrolidine

HRID 991856

Reaction equation

HRID 991856 reaction equation
CO[CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[C:10]([NH2:14])(=[O:13])[CH:11]=[CH2:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C2NC3C(=CC=CC=3)SC=2C=CC=1>CO>[N:4]1([CH2:3][NH:14][C:10](=[O:13])[CH:11]=[CH2:12])[CH2:8][CH2:7][CH2:6][C:5]1=[O:9]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6579AcrylamideHCID 7108PhenothiazineHCID 136248301-(Methoxymethyl)-2-pyrrolidinone

Product 1

HCID 18414899Acrylamidomethyl 2-oxopyrrolidineYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 65.6 g of 1-methoxymethyl-2-pyrrolidone, 75.5 g of acrylarnide, 0.20 g of p-toluene sulfonic acid and 0.20 g of phenothiazine was stirred under N2 atmosphere at 150° C. for 1 hour, during which time the methanol was removed by distillation. The residue was cooled, and recrystallized from acetone to give the title compound in a yield of 40%. mp: 73-74° C.

Workup

  1. customwas removed by distillation
  2. temperatureThe residue was cooled
  3. customrecrystallized from acetone

Sources & evidence

ORD record
ord-2c4bf1dc13d9444a977d82b3489b7370
Source dataset
uspto-grants-2002_10
Patent number
US06465588B1

Linked notes

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