HCID 10613276, compound → HCID 10165030, compound

HRID 2084417Notes

Reaction equation

HRID 2084417 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][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])=[CH:23][CH:22]=1>CN(C)C=O>[Cl:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([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:26][CH:25]=1

Participants

4

Reactant 2

HCID 10613276HCID 10613276, compoundHCID 22733335HCID 22733335, compound

Product 1

HCID 10165030HCID 10165030, 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-2,4-dichlorobiphenyl in N,N-dimethylformamide. Column chromatography provided an off-white solid. 1H NMR: δ 8.01 (v br s, 1H), 7.93 (dm, J=9.0 Hz, 2H), 7.47 (d, J=2.0 Hz, 1H), 7.22-7.35 (m, 6H), 7.07 (dm, J=9.0 Hz, 2H), 3.98 (a of ab, J=13.7 Hz, 1H), 3.93 (s, 3H), 3.40 (b of ab, J=13.7 Hz, 1H). MS (m/e): 519.9 (M−H)−. Anal: Calc for C23H17Cl2NO5S2.0.75 C4H10O: 54.03% C, 4.27% H, 2.42% N; Found: 53.63% C, 4.33% H, 2.23% N. MP: 104-107° C.

Workup

  1. customColumn chromatography provided an off-white solid

Sources & evidence

ORD record
ord-dadc96f4961843cfa38bb79da91d850f
Source dataset
uspto-grants-2004_04
Patent number
US06716862B2

Reaction notes

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