Chloromethyl phenyl sulphide → HCID 70046400, compound

HRID 1957414Notes

Reaction equation

HRID 1957414 reaction equation
[CH3:1][C:2]([C:5]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:6]=1[C:7](=[O:16])[NH:8][S:9]2(=[O:11])=[O:10])([CH3:4])[CH3:3].[C:17]1([S:23][CH2:24]Cl)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:17]1([S:23][CH2:24][N:8]2[C:7](=[O:16])[C:6]3[C:12](=[CH:13][CH:14]=[CH:15][C:5]=3[C:2]([CH3:1])([CH3:3])[CH3:4])[S:9]2(=[O:11])=[O:10])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 81623Chloromethyl phenyl sulphideHCID 159340764-tert-Butyl-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

Product 1

HCID 70046400HCID 70046400, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

The 4-(1,1-dimethylethyl)saccharin (0.025 g 1.0 mmol) was mixed with chloromethyl phenyl sulfide (0.25 g, 1.5 mmol) and tetrabutyl ammonium bromide (0.2 g, 0.6 mmol) in toluene (25 mL) and refluxed under nitrogen for 16 hr. The resulting mixture was cooled to room temperature, evaporated to dryness and purified by chromatography on silica gel (80%) MDC in hexanes) to give 0.35 g (98%) of 2-phenylthiomethyl-4-(1,1-dimethylethyl)saccharin, which was treated with sulfuryl chloride (0.25 g, 1.8 mmol) in MDC to give 0.21 g (75%) of 2-chloromethyl-4-(1,1-dimethylethyl)saccharin.

Workup

  1. temperaturerefluxed under nitrogen for 16 hr
  2. customevaporated to dryness
  3. custompurified by chromatography on silica gel (80%) MDC in hexanes)

Sources & evidence

ORD record
ord-fb63f357d4274550a9d350c595f8f3ef
Source dataset
uspto-grants-1998_07
Patent number
US05783589

Reaction notes

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