Phosphorus pentachloride → 5-Cyanoisatin chloride

HRID 1448905Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[O:13])#[N:2].P(Cl)(Cl)(Cl)(Cl)[Cl:15]>>[Cl-:15].[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[O:13])#[N:2]

Participants

Reactant 2

HCID 24819Phosphorus pentachloride

HCID 123514952,3-Dioxoindoline-5-carbonitrile

Product 1

HCID 203511125-Cyanoisatin chloride

Procedure

By reacting 5-cyanoisatin with phosphorous pentachloride, there is obtained 5-cyanoisatin chloride which, on reaction with 3(2H)-thianaphthenone, yields 5'-cyano-2'-indole-2-thianaphthenone indigo, which also is useful as a dyestuff.

Sources & evidence

ORD record: ord-b725e328ee914b218e4f05ddd9d02670
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04188325

Reaction notes

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