Dimethylformamide → 1,3-Benzothiazole-6-sulfonyl chloride

HRID 1391972Notes

Reaction equation

HRID 1391972 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

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 143978241,3-Benzothiazole-6-sulfonic acid

Product 1

HCID 27951701,3-Benzothiazole-6-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

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

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux
  3. customto yield a clear solution
  4. temperatureat reflux
  5. customthe solvent was removed in vacuo and excess HCl and thionyl chloride
  6. customwas chased by evaporation with dichloroethane

Sources & evidence

ORD record
ord-bdbc9d06d23747c0b443529dffa154eb
Source dataset
uspto-grants-2008_03
Patent number
US07339078B2

Reaction notes

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