Thiazolidinedione → HCID 14459864, compound

HRID 346189Notes

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 (m+), 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-d76bdd165dac4558b05511379d6bda22
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05061717

Reaction notes

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