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

HRID 2301014Notes

Reaction equation

HRID 2301014 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.C1(C)C=CC=CC=1.S(Cl)([Cl:22])=O>CN(C)C=O>[S:1]1[C:5]2[C:6]([C:10]([Cl:22])=[O:12])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 109211091,2,3-Benzothiadiazole-7-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

290 g of benzo-1,2,3-thiadiazole-7-carboxylic acid are suspended in 1.61 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. additionare added
  2. temperaturethe solution is cooled
  3. filtrationfiltered over a little Hyflo
  4. washthe residue is rinsed with toluene
  5. customthe filtrate is evaporated
  6. custom297 g (93%) of crude acid chloride, which can be further reacted directly
  7. customresult

Sources & evidence

ORD record
ord-7af315dd17bb41b4ba11b7d1a3ed0250
Source dataset
uspto-grants-2002_12
Patent number
US06498265B2

Reaction notes

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