Sodium Methoxide → HCID 117736901, compound

HRID 1504528Notes

Reaction equation

HRID 1504528 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][C:23]2[CH:28]=[C:27]([Cl:29])[C:26]([C:30]([F:33])([F:32])[F:31])=[CH:25][C:24]=2[O:34][CH3:35])=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][CH:10]=1)[N:22]([C:23]1[CH:28]=[C:27]([Cl:29])[C:26]([C:30]([F:32])([F:33])[F:31])=[CH:25][C:24]=1[O:34][CH3:35])[C:17](=[O:19])[CH:16]=[CH:15]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 117749293HCID 117749293, compound

Product 1

HCID 117736901HCID 117736901, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with (E)-ethyl 3-(5-(benzylthio)-2-((5-chloro-2-methoxy-4-(trifluoromethyl)phenyl)amino)phenyl)acrylate (5.33 g, 10.21 mmol) and MeOH (102 mL), followed by sodium methoxide (8.17 ml, 4.08 mmol) under nitrogen atmosphere. A reflux condensor was added, and the flask was lowered into an oil bath at 75° C. At 18 h the reaction was cooled to RT and filtered through a silica plug to remove black particulates. The product was eluted with MeOH and concentrated down to about 50 mL, followed by filtration through a medium glass frit, washing the solid with MeOH. The solid precipitate was dried under high vac to provide 6-(benzylthio)-1-(5-chloro-2-methoxy-4-(trifluoromethyl)phenyl)quinolin-2(1H)-one (3.257 g, 6.84 mmol, 67.0% yield). m/z (ESI) 475.8 (M+H)+.

Workup

  1. additionA reflux condensor was added
  2. customthe flask was lowered into an oil bath at 75° C
  3. filtrationfiltered through a silica plug
  4. customto remove black particulates
  5. washThe product was eluted with MeOH
  6. concentrationconcentrated down to about 50 mL
  7. filtrationfollowed by filtration through a medium glass frit
  8. washwashing the solid with MeOH
  9. customThe solid precipitate was dried under high vac

Sources & evidence

ORD record
ord-976771480fa143688ee0b74faf62219b
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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