Phthaloyl chloride → 2H-Isoindole-2-carbonitrile, 1,3-dihydro-1,3-dioxo-

HRID 2260461Notes

Reaction equation

HRID 2260461 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4](Cl)=[O:5].C[Si](C)(C)[N:15]=[C:16]=[N:17][Si](C)(C)C>CC1C=CC(C)=CC=1C.[Sn](Cl)(Cl)(Cl)Cl>[C:16]([N:17]1[C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]2[C:1]1=[O:11])#[N:15]

Participants

5

Reactant 2

HCID 6955Phthaloyl chlorideHCID 70473Bis(trimethylsilyl)carbodiimide

Product 1

HCID 109974912H-Isoindole-2-carbonitrile, 1,3-dihydro-1,3-dioxo-

Reagents, catalysts & solvents 2

HCID 24287Tin tetrachlorideCatalystHCID 72471,2,4-TrimethylbenzeneSolvent

Conditions

Temperature
60 °C

Procedure

N-Cyanophthalimide was prepared, as shown in Reaction 1, under a dry atmosphere from a 1:1 mixture of phthaloyl dichloride and 1,3-bis(trimethylsilyl) carbodiimide using 1,2,4-trimethylbenzene as solvent. Two drops of tin(IV) chloride were added as a catalyst before heating the mixture to 60° C. for six hours. The reaction mixture was cooled, filtered, and washed with chilled toluene giving yellow crystals as product. ##STR6##

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washwashed with chilled toluene giving yellow crystals as product

Sources & evidence

ORD record
ord-73d3b4413f384c17a188f0dce4fdd694
Source dataset
uspto-grants-1995_12
Patent number
US05478356

Reaction notes

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