Benzyl Bromide → 2-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743451Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of 4-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (8.25 g, 42.92 mmol) in 80 ml of dry DMF was added phenylmethyl bromide (8.08 g, 47.21 mmol) and tetrabutylammonium bromide (2.08 g, 6.64 mmol) in one portion. The resulting mixture was heated at 120° C. for 8 hours and then stirred at room temperature overnight. The mixture was cooled, poured over ice-water (400 ml), and the mixture was extracted with ethyl acetate (2×250 ml). The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The brown residual oil was purified by flash chromatography (silica gel; 25% ethyl acetate in hexane) to afford 9.34 g (77.1%) of 2-phenylmethyl-4-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IX: R1 =propyl; R2 =CH3) as an oil.

Workup

temperatureThe mixture was cooled
extractionthe mixture was extracted with ethyl acetate (2×250 ml)
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe brown residual oil was purified by flash chromatography (silica gel; 25% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-78d38e04959c4457b2512bf4346633f0
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556909

Reaction notes

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