2-Chloro-5-nitrobenzenesulfonic acid → 2-Chloro-5-nitrobenzenesulfonyl chloride

HRID 1599204Notes

Reaction equation

HRID 1599204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([OH:14])(=O)=[O:12].S(Cl)([Cl:17])=O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([Cl:17])(=[O:14])=[O:12]

Participants

4

Reactant 2

HCID 73102-Chloro-5-nitrobenzenesulfonic acidHCID 24386Thionyl Chloride

Product 1

HCID 206302-Chloro-5-nitrobenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2--Chloro-5-nitro benzene sulphonic acid (484 parts) was charged to a flask then quickly added thionyl chloride (1190 parts) and dimethyl formamide (12 parts). The resultant slurry was heated to 60° C. and stirred at 60°-65° C. for a total of 5 hours. The mixture was cooled to room temperature then poured onto ice/water. The precipitated solid was filtered off and washed with cold water before drying in vac oven to yield the product 2-chloro-5-nitro benzene sulphonylchloride (395 parts).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. additionthen poured onto ice/water
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with cold water
  5. custombefore drying in vac oven

Sources & evidence

ORD record
ord-c49e22226f7f4ebe8b674b49ed9b019c
Source dataset
uspto-grants-1998_04
Patent number
US05739299

Reaction notes

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