4-Cyanobenzenesulfonyl chloride → (Z)-4-cyano-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)benzenesulfonamide

HRID 517596Notes

Reaction equation

HRID 517596 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])/[C:7](=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)/[S:6][C:5]1=[O:20].[C:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)#[N:22].CCN(C(C)C)C(C)C.C(OC1C=CC(/C=C2/C(=O)N(CCNC(=O)C)C(=O)S/2)=CC=1)C>>[C:21]([C:23]1[CH:24]=[CH:25][C:26]([S:29]([NH:1][CH2:2][CH2:3][N:4]2[C:8](=[O:9])/[C:7](=[CH:10]/[C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=3)/[S:6][C:5]2=[O:20])(=[O:31])=[O:30])=[CH:27][CH:28]=1)#[N:22]

Participants

5

Reactant 4

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 45485995(Z)-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamide

Product 1

HCID 71697549(Z)-4-cyano-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)benzenesulfonamide

Procedure

The title compound 27b was prepared from compound 76 (101 mg, 0.25 mmol), 4-cyano-benzenesulfonyl chloride (55 mg, 0.28 mmol) and DIPEA (131 μL, 0.75 mmol) in a manner similar to that described for 25a in 92.0% (105 mg) yield as a light-yellow solid.

Workup

  1. customyield as a light-yellow solid

Sources & evidence

ORD record
ord-79e58ebdcc4f43e4b6f93a211baa9b35
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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