Thionyl Chloride → 2-Methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzoyl chloride

HRID 652757Notes

Reaction equation

HRID 652757 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:9]([S:15](=[O:18])(=[O:17])[NH2:16])=[C:8]([CH3:19])[C:4]=1[C:5](O)=[O:6].S(Cl)([Cl:22])=O>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:9]([S:15](=[O:18])(=[O:17])[NH2:16])=[C:8]([CH3:19])[C:4]=1[C:5]([Cl:22])=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl Chloride2×HCID 201968382-Methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzoic acid

Product 1

HCID 201968202-Methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

72 g of 2-methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzoic acid (0.25 mole), 250 ml of chloroform, 23 ml of thionyl chloride and 3 drops of dimethylformamide are placed in a 1 liter flask fitted with an agitator and a condenser. The mixture is heated to reflux for 1.5 hours, then 18 ml of thionyl chloride is added and the reflux is continued for 1.5 hours. The solids dissolve completely.

Workup

  1. customfitted with an agitator and a condenser
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 1.5 hours
  4. dissolutionThe solids dissolve completely

Sources & evidence

ORD record
ord-d2d56191e7bf4e59bfa653ea03ba0440
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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