Water → Methyl 4-(1,1-dioxo-isothiazolidin-2-yl)-3-methyl-benzoate

HRID 551194Notes

Reaction equation

HRID 551194 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH3:19])(=[O:7])=[O:6].[K].CC(C)([O-])C.O>CN(C=O)C>[O:6]=[S:5]1(=[O:7])[CH2:4][CH2:3][CH2:2][N:8]1[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 43654282Methyl 4-(3-chloro-propyl-sulphonyl-amino)-3-methyl-benzoateHCID 50987170Potassium tertbutoxide

Product 1

HCID 67048536Methyl 4-(1,1-dioxo-isothiazolidin-2-yl)-3-methyl-benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

370 mg (0.85 mmol) 70% methyl 4-(3-chloropropane-sulphonylamino)-3-methyl-benzoate dissolved in 26 ml DMF are combined with 275 mg (2.45 mmol) potassium-tert.-butoxide and stirred for 16 hours at ambient temperature. The reaction mixture is combined with water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate, evaporated down i. vac. and the residue is purified by chromatography on silica gel (eluant: dichloromethane/isopropanol 98:2).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. customevaporated down i
  4. customand the residue is purified by chromatography on silica gel (eluant: dichloromethane/isopropanol 98:2)

Sources & evidence

ORD record
ord-65accda2f26f4324b23ebe44e779b2d3
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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