Thionyl Chloride → 3-[3-(Chlorocarbonyl)benzene-1-sulfonyl]triaza-1,2-dien-2-ium-1-ide

HRID 259635Notes

Reaction equation

HRID 259635 reaction equation
[N:1]([S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11])(=[O:6])=[O:5])=[N+:2]=[N-:3].S(Cl)([Cl:18])=O>>[N:1]([S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([Cl:18])=[O:11])(=[O:6])=[O:5])=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 282899215980-11-7

Product 1

HCID 213906583-[3-(Chlorocarbonyl)benzene-1-sulfonyl]triaza-1,2-dien-2-ium-1-ideYield 75%

Conditions

Temperature
65 °C

Procedure

11.3 grams (50 milimoles) of 3-(azidosulfonyl) benzoic acid and 31 grams (261 milimoles) of thionyl chloride were added to a 200 ml. round bottom flask equipped with a magnetic stirrer, nitrogen sparge, reflux condenser and heating mantle. The mixture was stirred for 3 hours at 65° C. and then the excess thionyl chloride was stripped under vacuum. A 75 percent yield of 3-(azido-sulfonyl) benzoyl chloride was obtained and identified by spectroscopic analysis. Said benzoyl chloride was a straw-yellow liquid that slowly crystallized at room temperature and had a melting point of 41° C. and a refractive index of ND24.5 = 1.5751.

Workup

  1. customround bottom flask equipped with a magnetic stirrer
  2. customnitrogen sparge
  3. temperaturereflux condenser
  4. temperatureheating mantle

Sources & evidence

ORD record
ord-d3d29db043de4b3ab69a877b22abf892
Source dataset
uspto-grants-1977_07
Patent number
US04038456

Reaction notes

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