Dimethylformamide → 1,3-Benzothiazole-6-sulfonyl chloride
Reaction equation
S(Cl)([Cl:3])=O.[S:5]1[C:9]2[CH:10]=[C:11]([S:14]([OH:17])(=O)=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.CN(C)C=O>ClC(Cl)C>[Cl:3][S:14]([C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[CH:6][S:5][C:9]=2[CH:10]=1)(=[O:17])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Thionyl chloride (4 mL) was added to a suspension of the benzothiazole-6-sulfonic acid (0.60 g, 2.79 mmol) in dichloroethane (15 mL) and the reaction mixture was heated at reflux and dimethylformamide (5 mL) was added to the reaction mixture to yield a clear solution. After 1.5 hr. at reflux, the solvent was removed in vacuo and excess HCl and thionyl chloride was chased by evaporation with dichloroethane.
Workup
- temperaturethe reaction mixture was heated
- temperatureat reflux
- customto yield a clear solution
- temperatureat reflux
- customthe solvent was removed in vacuo and excess HCl and thionyl chloride
- customwas chased by evaporation with dichloroethane
Sources & evidence
- ORD record
- ord-679afb7de0c84e5997e01e80c7d10604
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091219B2
Reaction notes
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