Water → 2-(2-Thienylmethoxy)-1H-isoindole-1,3(2H)-dione

HRID 328445Notes

Reaction equation

HRID 328445 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].Cl[CH2:20][C:21]1[S:22][CH:23]=[CH:24][CH:25]=1.O>CS(C)=O>[S:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[CH2:20][O:7][N:8]1[C:9](=[O:18])[C:10]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]2[C:12]1=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 698302-(Chloromethyl)thiophene

Product 1

HCID 107064032-(2-Thienylmethoxy)-1H-isoindole-1,3(2H)-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Anhydrous potassium carbonate (11.04 g.) was added to a stirred suspension of N-hydroxyphthalimide (17.12 g.) in dry dimethyl sulphoxide (200 ml.). A brown colour developed, 2-chloromethylthiophene (28.5 g.) was added dropwise and the mixture was stirred for 16 hr., during which time the colour disappeared. The suspension was poured into water (800 ml.) and cooled to 5°. The white precipitate was filtered off, and recrystallised from ethanol to give colourless needles of N-(thien-2-ylmethoxy)phthalimide (23.4 g., 83%), m.p. 129.7°- 130.0° τ values (DMSO-d6) are 4.58 (CH2), 2.28, 2.68, 2.90 (thienyl protons), 2.08 (phthalimide protons).

Workup

  1. temperaturecooled to 5°
  2. filtrationThe white precipitate was filtered off
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-992182a419d4451aaf1eecfb7d95be91
Source dataset
uspto-grants-1977_04
Patent number
US04017515

Reaction notes

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