Tetrahydrofuran → 2,3-Dioxoindoline-5-carbonitrile

HRID 1413965Notes

Reaction equation

HRID 1413965 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].[C:7]([C:9]1[CH:10]=C2[C:15](=[CH:16][CH:17]=1)[NH:14]C(=S)C2C)#[N:8].[O:20]1CCCC1>>[C:7]([C:9]1[CH:10]=[C:1]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:3](=[O:20])[C:2]2=[O:4])#[N:8]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 194241955-Cyano-3-methylthiooxindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 123514952,3-Dioxoindoline-5-carbonitrileYield 35%

Procedure

According to the general procedure, using an equimolar amount of potassium t-butoxide, 0.62 g of 5-cyano-3-methylthiooxindole in 200 ml of dry tetrahydrofuran was stirred and aerated for 9 h at 0° C. and 15 h at 25° C. Acidification with 0.25 ml of conc. hydrochloric acid in 25 ml of water, followed by extraction with ether and standard workup (vide supra), gave an orange solid. Recrystallization from 95% ethanol gave 0.18 g (35% yield) of 5-cyanoisatin, mp 273°-274° C. (dec.).

Workup

  1. extractionAcidification with 0.25 ml of conc. hydrochloric acid in 25 ml of water, followed by extraction with ether and standard workup (vide supra)
  2. customgave an orange solid
  3. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-f4c4ee008cf448da974f7082d31cc2df
Source dataset
uspto-grants-1981_02
Patent number
US04252723

Reaction notes

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