Sodium Thiosulfate → HCID 18472671, compound

HRID 1277140Notes

Reaction equation

HRID 1277140 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:30])/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)[CH:18]=3)=[CH:9][CH:8]=2)[CH:2]=1.ClC1C=CC=C(C(OO)=[O:39])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[O-:39][N+:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:30])/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=4)[CH:18]=3)=[CH:11][CH:12]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 18472267HCID 18472267, compound

Product 1

HCID 18472671HCID 18472671, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-N-[4-(3-pyridyl)phenyl]-3-(4-methylphenyl)cinnamamide (250 mg) in tetrahydrofuran (20 ml) was added 3-chloroperbenzoic acid (70%, 0.24 g) at 0° C., and the mixture was stirred at room temperature for 18 hours. To the reaction mixture was added sodium thiosulfate solution, and the mixture was stirred for a few minutes and extracted with dichloromethane. The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The residue was recrystallized from ethanol-tetrahydrofuran-acetone to give (E)-N-[4-(1-oxidopyridin-3-yl)phenyl]-3-(4-methylphenyl)cinnamamide (Compound 193) (208 mg) as pale yellow crystals. 1H-NMR (200 MHz, DMSO-d6) δ 2.38 (3H, s), 6.95 (1H, d, J=15.7 Hz), 7.31 (2H, d, J=8.1 Hz), 7.45-7.57 (2H, m), 7.59-7.94 (12H, m), 8.19 (1H, d, J=6.5 Hz), 8.58 (1H, s). IR (KBr) 3423, 1672, 1597, 1531, 1477, 1340, 1201, 901, 835, 793 cm-1 ;

Workup

  1. stirringthe mixture was stirred for a few minutes
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethanol-tetrahydrofuran-acetone

Sources & evidence

ORD record
ord-aec2bc05cd034dada313f3fde7133eb5
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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