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Sodium Thiosulfate → 3-cyano-N-[2-(4-cyanophenyl)-4-oxobutyl]-N-methyl-1-naphthamide

HRID 749449
Notes
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Reaction equation

HRID 749449 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][CH:18]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[CH2:19][CH2:20][OH:21])[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][CH:18]([C:22]2[CH:23]=[CH:24][C:25]([C:28]#[N:29])=[CH:26][CH:27]=2)[CH2:19][CH:20]=[O:21])[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 689764513-cyano-N-[2-(4-cyanophenyl)-4-hydroxybutyl]-N-methyl-1-naphthamide

Product 1

HCID 112690383-cyano-N-[2-(4-cyanophenyl)-4-oxobutyl]-N-methyl-1-naphthamideYield 43%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 516892Sodium BicarbonateSolvent

Procedure

3-Cyano-N-[2-(4-cyanophenyl)-4-hydroxybutyl]-N-methyl-1-naphthamide (0.70 g, 1.8 mmol) was dissolved in CH2Cl2 (15 mL) and to the resultant solution was added Dess Martin Periodinane (0.85 g, 2.0 mmol) in portions. The mixture was stirred at room temperature overnight and then sodium thiosulfate (1.9 g, 12 mmol), dissolved in saturated NaHCO3 solution (30 mL), was added. The mixture was stirred vigorously for 2 h and then the organic solution was washed with brine and dried over Na2SO4. The solvent was removed by evaporation and the residue purified by flash chromatography (ethyl acetate-heptane, 4:1). There was obtained 0.50 g, (43%) of 3-cyano-N-[2-(4-cyanophenyl)-4-oxobutyl]-N-methyl-1-naphthamide as a white solid. 1H NMR (400 MHz, CDCl3): 2.7 (s, 3H), 2.9-4.4 (cm, 5H), 6.4-7.8 (cm, 8H), 7.9 (d, 1H), 8.2 (s, 1H), 9.8 (s, 1H); LCMS: m/z 382 (M+1)+.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred vigorously for 2 h
  3. washthe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed by evaporation
  6. customthe residue purified by flash chromatography (ethyl acetate-heptane, 4:1)

Sources & evidence

ORD record
ord-cd710ff6b9994fe7abe809df7a783698
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07402581B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes