2-Methylbenzenesulfonic acid → N-[(2-phthalimidoethoxy)methyl]acrylamide

HRID 255945

Reaktionsgleichung

Reaktionsgleichung von HRID 255945
OCC[C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]=12)=[O:8].[CH3:15][C:16](C(OC1[C@@]2(C)C(C)(C)[C@H](CC2)C1)=O)=C.C1(C)C(S(O)(=O)=O)=CC=CC=1.COC1C=CC(O)=CC=1.[OH:51][CH2:52][NH:53][C:54](=[O:57])[CH:55]=[CH2:56]>C(#N)C=C>[C:7]1(=[O:8])[N:9]([CH2:15][CH2:16][O:51][CH2:52][NH:53][C:54](=[O:57])[CH:55]=[CH2:56])[C:10](=[O:11])[C:5]2=[CH:4][CH:14]=[CH:13][CH:12]=[C:6]12

Komponenten

7

Edukt 5

HCID 69252-Methylbenzenesulfonic acidHCID 90154-MethoxyphenolHCID 13543N-MethylolacrylamideHCID 21422946HydroxyethylphthalimideHCID 71311141Isobornylmethacrylate2×

Produkt 1

HCID 13587414N-[(2-phthalimidoethoxy)methyl]acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7855AcrylonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Approximately equimolar amounts of N-(2-hydroxyethyl phthalimide (about 5 molar percent excess) and dried IBMA were mixed together in a reaction flask with 0.5 weight percent toluene sulfonic acid, based on the weight of IBMA, and 200 ppm MEHQ added. The nearly dry blend was stirred and heated using an external oil bath. When the temperature reached 65° C., a rapid reaction ensued and the reaction mixture partially liquified. After a short period of time, the reaction rate (as evidenced by the isobutyl alcohol removal) almost stopped, and the reaction mixture solidified. The reaction mixture was then rapidly heated to about 120° C., and the reaction again proceeded vigorously, going to near quantitative yields in a few more minutes. The product was a clear, low viscosity liquid at 120° C. which solidified at about 65° C. to a waxy, opaque white solid which was found to be readily soluble in acrylonitrile. The product was the 2-hydroxyethyl phthalimide ether of N-(hydroxymethyl) acrylamide.

Aufarbeitung

  1. additionadded
  2. temperatureheated
  3. customreached 65° C.
  4. customa rapid reaction
  5. waitAfter a short period of time
  6. customthe reaction rate (as evidenced by the isobutyl alcohol removal)
  7. customthe reaction
  8. customto near quantitative yields in a few more minutes
  9. customat 120° C.
  10. customsolidified at about 65° C. to a waxy, opaque white solid which

Quellen und Nachweise

ORD-Eintrag
ord-97b66427b0634bcbac763d5a84bd825d
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699965

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