m-Chloroperbenzoic acid → 3-{3-(3-Chloro-5-fluorophenyl)-5-[(1,1-dioxido-1,3-thiazolidin-3-yl)carbonyl]furan-2-yl}benzenecarbonitrile

HRID 2190135Notes

Reaction equation

HRID 2190135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][S:18](=[O:21])[CH2:17]3)=[O:15])[O:11][C:10]=2[C:22]2[CH:23]=[C:24]([C:28]#[N:29])[CH:25]=[CH:26][CH:27]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.ClC1C=C(C2C=C(C(N3CCSC3)=O)[O:40]C=2C2C=C(C#N)C=CC=2)C=C(F)C=1.ClC1C=CC=C(C(OO)=O)C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][S:18](=[O:40])(=[O:21])[CH2:17]3)=[O:15])[O:11][C:10]=2[C:22]2[CH:23]=[C:24]([C:28]#[N:29])[CH:25]=[CH:26][CH:27]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 468323003-[3-(3-Chloro-5-fluorophenyl)-5-(1,3-thiazolidin-3-ylcarbonyl)furan-2-yl]benzenecarbonitrileHCID 468325843-{3-(3-Chloro-5-fluorophenyl)-5-[(1-oxido-1,3-thiazolidin-3-yl)carbonyl]furan-2-yl}benzenecarbonitrile

Product 1

HCID 468325863-{3-(3-Chloro-5-fluorophenyl)-5-[(1,1-dioxido-1,3-thiazolidin-3-yl)carbonyl]furan-2-yl}benzenecarbonitrile

Procedure

The preparation of the title compound takes place in analogy to the synthesis of the compound from Example 3 starting with the compound from Example 1. Instead of 1.0 equivalent of meta-chloroperbenzoic acid, 2.2 equivalents are used. 80.0 mg (78% of theory) of the title compound are obtained.

Sources & evidence

ORD record
ord-69a7bef0e3ff4d4fb6a5263df76a802b
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

Loading…