Thiazolidinedione → HCID 14459864, compound

HRID 892814Notes

Reaction equation

[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[Li+].CCC[CH2-].[CH2:13]([N:20]([CH3:32])[S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1)(=[O:23])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1.O.Cl>[CH2:13]([N:20]([CH3:32])[S:21]([C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH:5]2[S:1][C:2](=[O:7])[NH:3][C:4]2=[O:6])=[CH:28][CH:29]=1)(=[O:23])=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2,4-Thiazolidinedione (11 mmol, 1.3 g) was dissolved in tetrahydrofuran (50 ml) and cooled to -78° C. N-Butyllithium (22 mmol, 13.8 ml of 1.6M in hexane) was added over 15 minutes. The cooling bath was removed and the reaction mixture was stirred for 20 minutes. N-Benzyl-N-methyl-4-(bromomethyl)benzenesulfonamide (10 mmol, 3.5 g) dissolved in tetrahydrofuran (50 ml) was added over 20 minutes. The reaction mixture was heated to reflux for 15 hours, cooled and diluted with water (50 ml) and 6N HCl (10 ml). The mixture was extracted with ethyl acetate (75 ml) and the organic layer was dried (Na2SO4) and removed in vacuo. The residue was purified on silica gel using 1:1 hexane:ethyl acetate to afford 3.0 g of title product as a gum; MS 390 (m30 ) 269, 205.

Workup

customThe cooling bath was removed
additionwas added over 20 minutes
temperatureThe reaction mixture was heated
temperatureto reflux for 15 hours
temperaturecooled
extractionThe mixture was extracted with ethyl acetate (75 ml)
dry with materialthe organic layer was dried (Na2SO4)
customremoved in vacuo
customThe residue was purified on silica gel using 1:1 hexane

Sources & evidence

ORD record: ord-2a183786514c497595c15632d336447e
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05120754

Reaction notes

Loading…