Chloromethyl phenyl sulphide → 2-Phenylthiomethyl-4-methylsaccharin

HRID 1957408Notes

Reaction equation

HRID 1957408 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:3]=1[C:4](=[O:13])[NH:5][S:6]2(=[O:8])=[O:7].[C:14]1([S:20][CH2:21]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:14]1([S:20][CH2:21][N:5]2[C:4](=[O:13])[C:3]3[C:9](=[CH:10][CH:11]=[CH:12][C:2]=3[CH3:1])[S:6]2(=[O:8])=[O:7])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 159340754-Methyl-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

Product 1

HCID 700447682-Phenylthiomethyl-4-methylsaccharinYield 46.3%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.0 g (0.005 mol) of 4-methylsaccharin, 0.33 g (0.001 mol) of TBAB and 1.2 g (0.0075 mol) of chloromethyl phenyl sulfide in 25 ml of toluene was heated under reflux for about sixteen hours and then cooled, diluted with ethyl acetate and the solution washed with aqueous bicarbonate and water. The organic layer was dried and taken to dryness to give 0.74 g of 2-phenylthiomethyl-4-methylsaccharin.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for about sixteen hours
  3. temperaturecooled
  4. washthe solution washed with aqueous bicarbonate and water
  5. customThe organic layer was dried

Sources & evidence

ORD record
ord-64e8433c9352484b910f4202543e4641
Source dataset
uspto-grants-1998_07
Patent number
US05783589

Reaction notes

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