Sodium Thiosulfate → 3-{3-(3-Chloro-5-fluorophenyl)-5-[(1-oxido-1,3-thiazolidin-3-yl)carbonyl]furan-2-yl}benzenecarbonitrile

HRID 2190134Notes

Reaction equation

HRID 2190134 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][CH2:17]3)=[O:15])[O:11][C:10]=2[C:21]2[CH:22]=[C:23]([C:27]#[N:28])[CH:24]=[CH:25][CH:26]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[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:37])[CH2:17]3)=[O:15])[O:11][C:10]=2[C:21]2[CH:22]=[C:23]([C:27]#[N:28])[CH:24]=[CH:25][CH:26]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 468323003-[3-(3-Chloro-5-fluorophenyl)-5-(1,3-thiazolidin-3-ylcarbonyl)furan-2-yl]benzenecarbonitrile

Product 1

HCID 468325843-{3-(3-Chloro-5-fluorophenyl)-5-[(1-oxido-1,3-thiazolidin-3-yl)carbonyl]furan-2-yl}benzenecarbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

95.0 mg (0.23 mmol) of the compound from Example 1 are provided in 3 ml of dichloromethane, and 51.6 mg (0.23 mmol) of meta-chloroperbenzoic acid are added. The mixture is stirred at room temperature overnight, a saturated aqueous sodium thiosulfate solution is subsequently added and the reaction mixture is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 63.0 mg (64% of theory) of the title compound are obtained.

Workup

  1. customthe reaction mixture is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-f338372759a74bcabf32989edde0117a
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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