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

HRID 267750Notes

Reaction equation

HRID 267750 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-ide

Conditions

Temperature
65 °C

Procedure

11.3 grams (50 milimoles) of 3-(azidosulfonyl) benzoic acid and 31 grams (261 millimoles) 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 per cent 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-6679fd63614944eea6185ab5f552e1f8
Source dataset
uspto-grants-1976_03
Patent number
US03944574

Reaction notes

Loading…