HCID 10613276, compound → HCID 10229820, compound

HRID 2084415Notes

Reaction equation

HRID 2084415 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]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[CH:23][CH:22]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:35])[F:36])[CH:28]=4)=[CH:25][CH:26]=3)[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10613276HCID 10613276, compoundHCID 21904153HCID 21904153, compound

Product 1

HCID 10229820HCID 10229820, 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-3-(trifluoromethyl)biphenyl in N,N-dimethylformamide. Column chromatography provided a light yellow glass. 1H NMR: δ 7.93 (dm, J=9.0 Hz, 2H), 7.78 (br s, 2H), 7.72 (d, J=7.5 Hz, 1H), 7.49-7.62 (m, 4H), 7.28 (dm, J=8.7 Hz, 2H), 7.07 (dm, J=9.0 Hz, 2H), 3.98 A of AB, J=13.7 Hz, 1H), 3.92 (s, 3H), 3.40 (B of AB, J=13.7 Hz, 1H). MS (m/e): 520.0 (M−H)−. Anal: Calc for C24H18F3NO5S2: 55.27% C, 3.48% H, 2.69% N; Found: 55.23% C, 3.70% H, 2.69% N.

Workup

  1. customColumn chromatography provided a light yellow glass

Sources & evidence

ORD record
ord-7b4d36573ee24a758a8472254bf4f27e
Source dataset
uspto-grants-2004_04
Patent number
US06716862B2

Reaction notes

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