Diethyl Ether → HCID 10182591, compound

HRID 2084413Notes

Reaction equation

HRID 2084413 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.C(OCC)C>CN(C)C=O>[C:21]1([CH2:20][C:12]2([S:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:10])=[O:11])[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 10613276HCID 10613276, compound

Product 1

HCID 10182591HCID 10182591, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 9 from from 5-(4-methoxybenzenesulfonyl)thiazolidine-2,4-dione and 4-(bromomethyl)biphenyl in N,N-dimethylformamide. Trituration with diethyl ether provided an off-white solid. 1H NMR: δ 7.98 (s, 1H), 7.93, (dd, J=7.0, 2.0 Hz, 2H), 7.34-7.57 (m, 7H), 7.23-7.26 (m, 2H), 7.06 (dd, J=7.0, 2.0 Hz, 2H), 3.97 (A of AB, J=13.7 Hz, 1H), 3.92 (s, 3H), 3.39 (B of AB, J=13.7 Hz, 1H). MS (m/e): 452.1 (M−H)−. Anal: Calc for C23H19NO5S2.C3H7NO: 59.30% C, 4.98% H, 5.32% N; Found: 59.13% C, 4.89% H, 5.24% N. MP: 119-122° C.

Sources & evidence

ORD record
ord-40724020f7744fc1823b31a99f8d0707
Source dataset
uspto-grants-2004_04
Patent number
US06716862B2

Reaction notes

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