Potassium Hydroxide → 2-(4-Cyclopropylpiperazin-1-yl)-6-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzothiazole

HRID 1944682Notes

Reaction equation

HRID 1944682 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([CH2:19][NH:20][S:21]([CH2:24][CH2:25][CH2:26]Cl)(=[O:23])=[O:22])[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[OH-].[K+]>CCO>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([CH2:19][N:20]5[CH2:26][CH2:25][CH2:24][S:21]5(=[O:23])=[O:22])[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 595887913-Chloropropane-1-sulfonic acid [2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]amide

Product 1

HCID 595887992-(4-Cyclopropylpiperazin-1-yl)-6-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzothiazoleYield 70.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-chloropropane-1-sulfonic acid [2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylmethyl]amide (300 mg, 0.70 mmol) and potassium hydroxide (396 mg, 7.0 mmol) in EtOH (5 mL) was heated at reflux for 1 h. The volatiles were evaporated and the residue was extracted with CH2Cl2, washed with brine and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (elute: 5% CH2Cl2 in methanol) to give 2-(4-cyclopropylpiperazin-1-yl)-6-(1,1-dioxo-1λ6-isothiazolidin-2-ylmethyl)benzothiazole 193 mg (49%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customThe volatiles were evaporated
  4. extractionthe residue was extracted with CH2Cl2
  5. washwashed with brine
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography on silica gel (elute: 5% CH2Cl2 in methanol)

Sources & evidence

ORD record
ord-8b69bd30754d42a49b18573a7a55e9cc
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

Loading…