Thionyl Chloride → 9-Oxo-9H-thioxanthene-3-carbonitrile 10,10-dioxide

HRID 867202Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8](=[O:20])[C:9]3[C:14]([S:15](=[O:19])(=[O:18])[C:16]=2[CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)(=O)[NH2:2].S(Cl)(Cl)=O>CN(C)C=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8](=[O:20])[C:9]3[C:14]([S:15](=[O:18])(=[O:19])[C:16]=2[CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)#[N:2]

Participants

Conditions

Temperature: -10 °C

Procedure

3-Carbamoylthioxanthone-10,10-dioxide (32.5 g) was dissolved in dimethyl formamide (ca. 1 liter) and cooled to -10° C. in a solid carbon dioxide ethanol bath. Thionyl chloride (80 ml) was then added dropwise over 0.5 hour, maintaining the internal temperature at -5° to -10° C. Stirring was continued at this temperature for a further 2 hours. The reaction mixture was then poured into ice-water. The precipitated solid was filtered off, washed well with water, and dried at 100° C. The resulting 3-cyanothioxanthone-10,10-dioxide had a melting point of 282°-283° C.

Workup

temperaturemaintaining the internal temperature at -5° to -10° C
filtrationThe precipitated solid was filtered off
washwashed well with water
customdried at 100° C

Sources & evidence

ORD record: ord-8058dca0b8b7498a9c120a4831540efe
Source dataset: uspto-grants-1978_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04103015

Reaction notes

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