Thionyl Chloride → 2-(1,2,3-Thiadiazol-5-yl)-1H-isoindole-1,3(2H)-dione

HRID 2263284Notes

Reaction equation

HRID 2263284 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12]/[CH:13]=[N:14]/[NH:15]C(OCC)=O.[S:21](Cl)(Cl)=O>>[S:21]1[C:12]([N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])=[CH:13][N:14]=[N:15]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 14248291HCID 14248291, compound

Product 1

HCID 687779632-(1,2,3-Thiadiazol-5-yl)-1H-isoindole-1,3(2H)-dioneYield 59.9%

Procedure

Ethyl (2E)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethylidene]hydrazinecarboxylate (612 mg, 2.22 mmol) was slowly added to thionyl chloride (1.5 ml), and the mixture was stirred for 1 day. Crystals were collected by filtration and washed with ethyl acetate to give 308 mg (59.9%) of the desired product as a solid.

Workup

  1. filtrationCrystals were collected by filtration
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-5ecc681cdfc24fedbe037ba9711d6c28
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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