4-Cyanophenol → HCID 11805868, compound

HRID 1191060Notes

Reaction equation

HRID 1191060 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)#[N:4].[CH3:12][N:13]([CH3:17])[C:14](Cl)=[S:15]>O>[CH3:12][N:13]([CH3:17])[C:14]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[CH:6][CH:7]=1)=[S:15]

Participants

5

Reactant 3

HCID 130194-CyanophenolHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chloride

Product 1

HCID 11805868HCID 11805868, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add sodium hydride (1.21 g, 95%) to a solution of 4-cyanophenol (5.71 g, 47.98 mmol) in anhydrous TI-IF (70 mL) and stir the mixture for 5 min. Add dimethylthiocarbamoyl chloride (5.93 g, 47.98 mmol) and heat the mixture at reflux for 3 h. Cool the mixture to room temperature and add water. Extract the aqueous phase with EtOAc, dry the organic phase over MgSO4, filter and concentrate in vacuo to obtain a solid. Wash the solid with diethyl ether, filter and dry in vacuo to obtain the desired intermediate as a solid (4.41 g, 75%).

Workup

  1. temperatureat reflux for 3 h
  2. extractionExtract the aqueous phase with EtOAc
  3. dry with materialdry the organic phase over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customto obtain a solid
  7. washWash the solid with diethyl ether
  8. filtrationfilter
  9. customdry in vacuo

Sources & evidence

ORD record
ord-4c0a99a32c55495fbf1fd57316a7fcaf
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…