Chloromethyl phenyl sulphide → HCID 70046400, compound

HRID 864720Notes

Reaction equation

HRID 864720 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 0.21g (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-6407fad0d15b4640923ff80fccac6d9e
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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