Dichloromethane → 3-Amino-4-hydroxy-1,2-benzoisothiazole-1,1-dioxide

HRID 1995382Notes

Reaction equation

HRID 1995382 reaction equation
[NH2:1][C:2]1[C:6]2[C:7]([O:11]C)=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:14])(=[O:13])[N:3]=1.[C-]#N.[K+].C(Cl)Cl>CS(C)=O>[NH2:1][C:2]1[C:6]2[C:7]([OH:11])=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:14])(=[O:13])[N:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 155671643-Amino-4-methoxy-1,2-benzoisothiazole-1,1-dioxide

Product 1

HCID 1363022813-Amino-4-hydroxy-1,2-benzoisothiazole-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5 gm of 3-amino-4-methoxy-1,2-benzoisothiazole-1,1-dioxide and 1.63 gm of potassium cyanide in 15 ml of dimethyl-sulfoxide was heated to 130°-140° C. (bath temperature 160° C.) and kept at this temperature for 1.5 hours. After cooling, the reaction mixture was stirred into 250 ml of methylene chloride, and the resulting precipitate was filtered off, dried and dissolved in 30 ml of water. At 60° C. the solution was treated with charcoal and filtered while hot. The hot filtrate was adjusted to pH 1 with concentrated aqueous hydrochloric acid. After cooling, the resulting crystals were suction-filtered off, washed with a little ice water and dried in vacuo.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was filtered off
  3. customdried
  4. dissolutiondissolved in 30 ml of water
  5. additionAt 60° C. the solution was treated with charcoal
  6. filtrationfiltered while hot
  7. temperatureAfter cooling
  8. filtrationthe resulting crystals were suction-filtered off
  9. washwashed with a little ice water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-a6ab749628a14907b99029626d4a4cd8
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

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