Chloromethyl phenyl sulphide → 1,1-Dioxo-2-propan-2-yl-1,2-benzothiazol-3-one

HRID 1768694Notes

Reaction equation

HRID 1768694 reaction equation
C([C:4]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:5]=1[C:6](=[O:15])[NH:7][S:8]2(=[O:10])=[O:9])(C)C.ClCS[C:19]1[CH:24]=CC=C[CH:20]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:19]([N:7]1[C:6](=[O:15])[C:5]2[C:11](=[CH:12][CH:13]=[CH:14][CH:4]=2)[S:8]1(=[O:9])=[O:10])([CH3:24])[CH3:20]

Participants

5

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 117701284-Isopropylsaccharin

Product 1

HCID 2365421,1-Dioxo-2-propan-2-yl-1,2-benzothiazol-3-oneYield 141.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-isopropylsaccharin (37.9 g), phenyl chloromethyl sulfide (33.3 g), tetrabutylammonium bromide (5.4 g) and toluene (200 mL) was heated under reflux for 24 hours, then stripped of volatiles. Column chromatography of the residue on silica gel (485 g) and elution first with hexane, then hexane-dichloromethane (1:1), then dichloromethane gave in the hexane-dichloromethane eluate 2-phenylthiomethyl-4,-isopropylsaccharin as a pale yellow oil (53.5 g, 92% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. washColumn chromatography of the residue on silica gel (485 g) and elution first with hexane
  4. customhexane-dichloromethane (1:1), then dichloromethane gave in the hexane-dichloromethane eluate 2-phenylthiomethyl-4

Sources & evidence

ORD record
ord-b5f6fb6792dc4b9588788b02257347e5
Source dataset
uspto-grants-1995_01
Patent number
US05378720

Reaction notes

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