Hydrochloric Acid → HCID 178515053, compound

HRID 596966Notes

Reaction equation

HRID 596966 reaction equation
[C:1]([C:3]1[C:16]2[S:15](=[O:18])(=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2].[N-:20]=[N+:21]=[N-:22].[Na+].Cl>CS(C)=O>[NH:20]1[C:1]([C:3]2[C:16]3[S:15](=[O:17])(=[O:18])[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8](=[O:19])[C:7]=3[CH:6]=[CH:5][CH:4]=2)=[N:2][N:22]=[N:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 10492181HCID 10492181, compound

Product 1

HCID 178515053HCID 178515053, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Cyanothioxanthone-10,10-dioxide (1.35g), sodium azide (0.39g) ammonium chloride (0.32g) and dimethylsulphoxide were heated together at 125°- 130° C. for 6.5 hr. The mixture was cooled, poured into dilute hydrochloric acid and the precipitated product filtered off. It was warmed with 1% sodium bicarbonate solution, filtered, and the filtrate acidified with dilute hydrochloric acid. 4-(5-Tetrazolyl)thioxanthone-10,10-dioxide was filtered off and recrystallised from acetic acid, m.p. 271° C. with decomposition. Found: C 53.50%; H 2.70%; N 18.04%. C14H8N4O3S requires C 53.85%; H 2.58%; N 17.95%.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitated product filtered off
  3. temperatureIt was warmed with 1% sodium bicarbonate solution
  4. filtrationfiltered
  5. filtration4-(5-Tetrazolyl)thioxanthone-10,10-dioxide was filtered off
  6. customrecrystallised from acetic acid, m.p. 271° C. with decomposition

Sources & evidence

ORD record
ord-1ab5a5655b2048cfaeec3c5348fef83e
Source dataset
uspto-grants-1977_03
Patent number
US04012499

Reaction notes

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