Acrylic Acid → 2-Propenoic acid, 2,5-dioxo-1-pyrrolidinyl ester

HRID 2285583Notes

Reaction equation

HRID 2285583 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9](O)(=[O:12])[CH:10]=[CH2:11]>C(Cl)(Cl)Cl>[C:9]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])(=[O:12])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 1815082-Propenoic acid, 2,5-dioxo-1-pyrrolidinyl esterYield 68.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 400 ml of chloroform, 115 g of N-hydroxysuccinimide and 72 g of acrylic acid in a reaction vessel, 206 g of N,N-dicyclohexylcarbodiimide dissolved in 100 ml of chloroform was added dropwise over a period of 2 hours under cooling with ice water. Following a 2-hour stirring at room temperature, the precipitate was filtered off and the filtrate concentrated at low temperature for crystallization. The resulting crystals were filled to give 116 g of N-acryloyloxysuccinimide (mp=61°-62° C., yield=68%). The active ester content was determined by the method of Ronald L. Schnaar and Yuan Chuan Lee described in Biochemistry, p. 1535 (1975) as 5.2×10-3 eq./g.

Workup

  1. additionwas added dropwise over a period of 2 hours
  2. waitFollowing a 2-hour
  3. filtrationthe precipitate was filtered off
  4. concentrationthe filtrate concentrated at low temperature for crystallization
  5. additionThe resulting crystals were filled

Sources & evidence

ORD record
ord-e590481eeff94e12aede46171fc03452
Source dataset
uspto-grants-1982_04
Patent number
US04323644

Reaction notes

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