Dimethylformamide → 1,2,3-Benzothiadiazole-7-carbonyl chloride

HRID 1457287Notes

Reaction equation

HRID 1457287 reaction equation
[S:1]1[C:5]2[C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.CN(C)C=O.S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[S:1]1[C:5]2[C:6]([C:10]([Cl:20])=[O:12])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 109211091,2,3-Benzothiadiazole-7-carboxylic acid

Product 1

HCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

290 g of benzo-1,2,3-thiadiazole-7-carboxylic acid are suspended in 1.6 l of toluene, 3.5 ml of dimethylformamide and 129 ml of thionyl chloride are added and the mixture is stirred at 80°-90° C., the suspension turning into a solution as the release of gas progresses. When the reaction has ended, the solution is cooled and filtered over a little Hyflo, the residue is rinsed with toluene and the filtrate is evaporated. 297 g (93%) of crude acid chloride, which can be further reacted directly, result.

Workup

  1. temperaturethe solution is cooled
  2. filtrationfiltered over a little Hyflo
  3. washthe residue is rinsed with toluene
  4. customthe filtrate is evaporated
  5. custom297 g (93%) of crude acid chloride, which can be further reacted directly
  6. customresult

Sources & evidence

ORD record
ord-d997d61c8ec64cb1bc1f122fd2bf2cde
Source dataset
uspto-grants-1998_12
Patent number
US05847147

Reaction notes

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