Chloromethyl phenyl sulphide → 2-Phenylthiomethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743460Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (2.5 g, 9.81 mmol), phenylthiomethyl chloride (2.18 g, 13.74 mmol) and tetrabutylammonium bromide (0.369 g, 1.145 mmol) suspended in 150 ml of DMF was heated at 100° C. for 18 hours. After adding additional TBAB (0.369 g), the mixture was stirred at 95° C. for 4 hours, cooled, and poured into ice/water. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with water and brine, and dried over sodium sulfate. The organic layer was concentrated in vacuo and the residue was purified by silica column chromatography (15% ethyl acetate in hexane) to afford 1.396 g (39%) of 2-phenylthiomethyl-4- (3-methyl-3-chlorobutyl) -5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =(CH2)2C(Cl) (CH3)2 ; R3 =CH3) as a solid.

Workup

temperaturecooled
extractionThe reaction mixture was extracted with ethyl acetate
washthe organic layer was washed with water and brine
dry with materialdried over sodium sulfate
concentrationThe organic layer was concentrated in vacuo
customthe residue was purified by silica column chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-221f44519ae84d0e8d0c4ef43403f456
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556909

Reaction notes

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