Diethyl Ether → HCID 10117133, compound

HRID 2084414Notes

Reaction equation

HRID 2084414 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][CH:28]=2)=[CH:23][CH:22]=1.C(OCC)C>CN(C)C=O>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:24]2[CH:25]=[CH:26][C:21]([CH2:20][C:12]3([S:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)(=[O:10])=[O:11])[S:16][C:15](=[O:17])[NH:14][C:13]3=[O:18])=[CH:22][CH:23]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10613276HCID 10613276, compoundHCID 12786364HCID 12786364, compound

Product 1

HCID 10117133HCID 10117133, 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-4-chlorobiphenyl in N,N-dimethylformamide. Trituration with diethyl ether provided an off-white solid. 1H NMR: δ 7.99 (s, 1H), 7.93 (dm, J=9.0 Hz, 2H), 7.45-7.49 (m, 4H), 7.38-7.41 (m, 2H), 7.23-7.26 (m, 2H), 7.06 (dm, J=9.0 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): 486.0 & 488.0 (M−H)−Cl isotopes. Anal: Calc for C23H18ClNO5S2.C3H7NO: 55.66% C, 4.49% H, 4.99% N; Found: 55.57% C, 4.41% H, 4.85% N. MP: 197-200° C.

Sources & evidence

ORD record
ord-0ba3fa69ad6a49aa9516cf81cac246c6
Source dataset
uspto-grants-2004_04
Patent number
US06716862B2

Reaction notes

Loading…