Thionyl Chloride → 5-(Aminosulphonyl)-2,3-dimethoxybenzoyl chloride

HRID 1194746Notes

Reaction equation

HRID 1194746 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:8][C:4]=1[C:5](O)=[O:6].S(Cl)([Cl:20])=O>CCCCCC>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:8][C:4]=1[C:5]([Cl:20])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 30176982,3-Dimethoxy-5-sulphamoylbenzoic acid

Product 1

HCID 937835-(Aminosulphonyl)-2,3-dimethoxybenzoyl chlorideYield 94.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

419 g (1.6 mole) of 2,3-dimethoxy-5-sulphamoyl benzoic acid and 1,351 g (11.35 moles) of thionyl chloride are placed in a 2 liter flask fitted with an agitator, a thermometer and a condenser connected to a soda bubbler. The mixture is brought to reflux for 1 hour, after which the excess thionyl chloride is expelled under vacuum. The residue is dissolved in 1,000 ml of hexane, filtered, washed twice with 500 ml of petroleum ether and dried in a desiccator under vacuum. 424 g (yield 94.8%) of 2,3-dimethoxy-5-sulphamoyl benzoyl chloride is obtained with a melting point of 153° C.

Workup

  1. customfitted with an agitator
  2. temperatureto reflux for 1 hour
  3. filtrationfiltered
  4. washwashed twice with 500 ml of petroleum ether
  5. customdried in a desiccator under vacuum

Sources & evidence

ORD record
ord-81ecc167ba56441898e77e3f5f1dc798
Source dataset
uspto-grants-1989_03
Patent number
US04816471

Reaction notes

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