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

HRID 255945

反応式

HRID 255945 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7855Acrylonitrile溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97b66427b0634bcbac763d5a84bd825d
出典データセット
uspto-grants-1987_10
特許番号
US04699965

関連ノート

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