Diisopropylethylamine → N-[(5-Methyl-2-phenyl-4-oxazolyl)methyl]-4-[(thiazolidine-2,4-dion-5-yl)methyl]benzenesulfonamide

HRID 1729047Notes

Reaction equation

[S:1]1[CH:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=2)[C:4](=[O:17])[NH:3][C:2]1=[O:18].[CH3:19][C:20]1[O:24][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH2:31][NH2:32].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:19][C:20]1[O:24][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH2:31][NH:32][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:5]2[S:1][C:2](=[O:18])[NH:3][C:4]2=[O:17])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

4-[(Thiazolidine-2,4-dion-5-yl)methyl]benzenesulfonyl chloride (1.62 g, 5.31 mmol) in 25 mL of CH2Cl2 was cooled to 0° C. N-[(5-Methyl-2-phenyl-4-oxazolyl)methyl]amine (1.0 g, 5.31 mmol) in 10 mL of CH2Cl2 was added dropwise, followed by diisopropylethylamine(1.1 mL, 6.37 mmol) and the mixture stirred at 0° C. for 20 minutes,then at room temperature for 18 hours. The reaction mixture was diluted with 20 mL CH2Cl2, washed 3×25 mL 1N HCl, 1×25 mL 5% NaHCO3 and 2×25 mL brine, dried (MgSO4) and stripped to1.9 g of solids. The latter was flash chromatographed on silica gel using 3:40 ethyl acetate:hexane as eluant to yield 0.34 g of purified, present title product, mp 120°-122° C.

Workup

waitat room temperature for 18 hours
washwashed 3×25 mL 1N HCl, 1×25 mL 5% NaHCO3 and 2×25 mL brine
dry with materialdried (MgSO4)
customchromatographed on silica gel using 3:40 ethyl acetate
customhexane as eluant to yield 0.34 g
customof purified

Sources & evidence

ORD record: ord-49bad1fee20443fe8196dd848c54a42d
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05330998

Reaction notes

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