Diethyl Ether → HCID 10281940, compound

HRID 2084416Notes

Reaction equation

HRID 2084416 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]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)=[CH:23][CH:22]=1.C(OCC)C>CN(C)C=O>[F:34][C:33]([F:35])([F:36])[C:31]1[CH:32]=[C:27]([CH:28]=[C:29]([C:37]([F:40])([F:38])[F:39])[CH:30]=1)[C:24]1[CH:25]=[CH:26][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:22][CH:23]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10613276HCID 10613276, compoundHCID 22733341HCID 22733341, compound

Product 1

HCID 10281940HCID 10281940, 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-3,5-bis(trifluoromethyl)biphenyl in N,N-dimethylformamide. Trituration with diethyl ether provided a white solid. 1H NMR: δ 8.43 (br s, 1H), 7.91-7.99 (m, 4H), 7.85 (s, 1H), 7.53 (dd, J=6.5, 1.8 Hz, 2H), 7.33 (d, J=8.3 Hz, 2H), 7.07 (dm, J=9.0 Hz, 2H), 4.00 (A of AB, J=13.7 Hz, 1H), 3.93 (s, 3H), 3.42 (B of AB), J=13.7 Hz, 1H). MS (m/e): 588.5 (M−H)−. Anal: Calc for C25H17F6NO5S2.C3H7NO: 50.75% C, 3.65% H, 4.23% N; Found: 50.70% C, 3.60% H, 4.01% N. MP: 122-125° C.

Sources & evidence

ORD record
ord-5d5791f86f1743eb8fab722f966311be
Source dataset
uspto-grants-2004_04
Patent number
US06716862B2

Reaction notes

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