Water → Dichlobentiazox

HRID 2236116Notes

Reaction equation

HRID 2236116 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:12])(=[O:11])[N:3]=1.[Cl:13][C:14]1[C:18]([Cl:19])=[C:17]([CH2:20][OH:21])[S:16][N:15]=1.C(N(CC)CC)C.O>C(#N)C>[Cl:13][C:14]1[C:18]([Cl:19])=[C:17]([CH2:20][O:21][C:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[S:4](=[O:12])(=[O:11])[N:3]=2)[S:16][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 64783Pseudosaccharin chlorideHCID 16723166(3,4-Dichloroisothiazol-5-yl)methanol

Product 1

HCID 17756624DichlobentiazoxYield 82.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 6 ml of acetonitrile were dissolved 0.62 g (3.10 mmol) of 3-chloro-1,2-benzoisothiazole 1,1-dioxide and 0.57 g (3.10 mmol) of the (3,4-dichloroisothiazol-5-yl)methanol. To the resulting solution was dropwise added 0.34 g (3.4 mmol) of triethylamine, followed by stirring at room temperature for 5 hours to give rise to a reaction. After the completion of the reaction, 12 ml of water was added. The resulting crystals were obtained by filtration. The crystals were washed with water and isopropyl alcohol to obtain 0.89 g (yield: 82%) of 3-(3,4-dichloroisothiazol-5-ylmethoxy)-1,2-benzoisothiazole 1,1-dioxide as a colorless powder (melting point: 165 to 167° C.).

Workup

  1. customto give rise
  2. customto a reaction
  3. additionwas added
  4. customThe resulting crystals were obtained by filtration
  5. washThe crystals were washed with water and isopropyl alcohol

Sources & evidence

ORD record
ord-87cfdb9d30a44fab894dfce451049edf
Source dataset
uspto-grants-2010_05
Patent number
US07714140B2

Reaction notes

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