Dimethylformamide dimethyl acetal → (E)-2-[4-[4-[3-(dimethylamino)-1-oxo-2-propenyl]phenoxy]butyl]-1H-isoindole-1,3(2H)-dione

HRID 1417320Notes

Reaction equation

HRID 1417320 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:28](OC)[N:29]([CH3:31])[CH3:30]>O1CCOCC1>[CH3:28][N:29]([CH3:31])/[CH:30]=[CH:2]/[C:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:14](=[O:23])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]2=[O:22])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 675980872-[4-(4-Acetylphenoxy)butyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 67693872(E)-2-[4-[4-[3-(dimethylamino)-1-oxo-2-propenyl]phenoxy]butyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 25 g of 2-[4-(4-acetylphenoxy)butyl]-1H-isoindole-1,3(2H)-dione (Example 42) and 25 ml of dimethylformamide dimethylacetal in 50 ml of dioxane is heated in the steam bath for 16 hours. The volatile components are removed in vacuo, a tacky reddish-brown solid being obtained. A portion is recrystallized from dichloromethane/hexane; m.p. 109°-111° C.

Workup

  1. customThe volatile components are removed in vacuo
  2. customa tacky reddish-brown solid being obtained
  3. customA portion is recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-aac7f422b5394a79a857d7563deeafd2
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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