Chloromethyl phenyl sulphide → HCID 70044820, compound

HRID 266445Notes

Reaction equation

HRID 266445 reaction equation
[Br: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].CC(C)([O-])C.[K+].[C:20]1([S:26][CH2:27]Cl)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:3]=1[C:4](=[O:13])[N:5]([CH2:27][S:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:6]2(=[O:8])=[O:7]

Participants

7

Reactant 3

HCID 81623Chloromethyl phenyl sulphideHCID 14257493133743-22-3HCID 23665647Potassium tert-butoxide

Product 1

HCID 70044820HCID 70044820, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.27 g (0.012 mol) of 4-bromosaccharin [Japanese Pat. Publcn. 58/79,034, published May 12, 1983; C. A. 100, 7773w (1984)], 1.63 g (0.015 mol) of potassium t-butoxide, 0.39 g (0.0012 mol) of tetrabutylammonium bromide and 3.0 ml (0.022 mol) of chloromethyl phenyl sulfide in 100 ml of toluene was heated under reflux under a nitrogen atmosphere for eight hours and then at ambient temperature for about sixteen hours. The reaction mixture was then cooled, diluted with ethyl acetate and the organic layer washed with bicarbonate, water and brine and then dried over magnesium sulfate and taken to dryness in vacuo. The residual solid was recrystallized from toluene-hexane to give 3.86 g (84%) of 4-bromo-2-phenylthiomethylsaccharin, mp 174.5°-178° C.

Workup

  1. temperatureunder reflux under a nitrogen atmosphere for eight hours
  2. waitat ambient temperature for about sixteen hours
  3. temperatureThe reaction mixture was then cooled
  4. washthe organic layer washed with bicarbonate, water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe residual solid was recrystallized from toluene-hexane

Sources & evidence

ORD record
ord-03e9ebc55f2f4b84976700a702e8865d
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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