Diethyl Ether → HCID 10299362, compound

HRID 2084412Notes

Reaction equation

HRID 2084412 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][C:28]=2[C:33]#[N:34])=[CH:23][CH:22]=1.C(OCC)C>CN(C)C=O>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=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)#[N:34]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 10613276HCID 10613276, compound

Product 1

HCID 10299362HCID 10299362, 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-cyanobiphenyl in N,N-dimethylformamide. Trituration with diethyl ether provided an off-white solid. 1H NMR: δ 7.93 (dd, J=7.0, 2.0 Hz, 2H), 7.75 (dd, J=7.7, 1.0 Hz, 1H), 7.64 (dt, J=1.3, 7.7 Hz, 1H), 7.42-7.50 (m, 4H), 7.31 (d, J=8.3 Hz, 2H), 7.07 (dd, J=7.1, 1.9 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): 477.3 (M−H)+. Anal: Calc for C24H18N2O5S2.0.167 C3H9NO: 59.92% C, 4.00% H, 6.18% N; Found: 59.60% C, 4.04% H, 5.99% N.

Sources & evidence

ORD record
ord-089025f1ba3d45cdbc8a7db24732f5e2
Source dataset
uspto-grants-2004_04
Patent number
US06716862B2

Reaction notes

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