Thionyl Chloride → HCID 86741590, compound

HRID 652777Notes

Reaction equation

HRID 652777 reaction equation
[CH3:1][O:2][CH:3]1[C:11](=[S:12](=[O:14])=[O:13])[C:10]([O:15][CH3:16])=[C:9]([CH3:17])[CH:8]=[C:4]1[C:5](O)=[O:6].S(Cl)([Cl:20])=O>CN(C)C=O>[CH3:1][O:2][CH:3]1[C:11](=[S:12](=[O:14])=[O:13])[C:10]([O:15][CH3:16])=[C:9]([CH3:17])[CH:8]=[C:4]1[C:5]([Cl:20])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86741591HCID 86741591, compound

Product 1

HCID 86741590HCID 86741590, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

161 g of 2,4-dimethoxy-5-methyl sulphonyl-benzoic acid is reacted. 590 g of thionyl chloride, 5 drops of dimethylformamide and about half of the organic acid are placed in a 2 liter flask filtered with a reflux condenser. The resultant suspension is heated in a water bath at 55° for about 5 minutes. The second half of the organic acid is added and heating is continued for 20 minutes at 60°-65° then for 45 minutes at 70°-75°. The medium becomes fluid and turns yellow. The acid dissolves gradually, while the acid chloride begins to crystallise. When the reaction is over the excess thionyl chloride is distilled to constant weight, finishing up under vacuum.

Workup

  1. filtrationfiltered with a reflux condenser
  2. temperatureThe resultant suspension is heated in a water bath at 55° for about 5 minutes
  3. additionThe second half of the organic acid is added
  4. temperatureheating
  5. waitfor 45 minutes at 70°-75°
  6. dissolutionThe acid dissolves gradually, while the acid chloride
  7. customto crystallise
  8. distillationis distilled to constant weight

Sources & evidence

ORD record
ord-55f0f95a27e14c1ca8a95b2136e86ab3
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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