Potassium Carbonate → HCID 58495561, compound

HRID 1190962Notes

Reaction equation

HRID 1190962 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1)#[N:2].S(C1C=CC(C)=CC=1)(O[CH:14]1[CH2:19][CH2:18][CH2:17][C:16]([CH3:21])([CH3:20])[CH2:15]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:20][C:16]1([CH3:21])[CH2:17][CH2:18][CH2:19][CH:14]([S:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:15]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5850584-ThiobenzonitrileHCID 15254221HCID 15254221, compound

Product 1

HCID 58495561HCID 58495561, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-cyanothiophenol (1 g, 7.4 mmol) in DMF (15 mL) add 3,3-dimethylcyclohexyl tosylate (2.06 g, 7.4 mmol) and potassium carbonate (3.06 g, 22.2 mmol), and warm to 60° C. for 18 h. Dilute the mixture with EtOAc (50 mL) and wash sequentially with water (3×50 mL), saturated aqueous NaHCO3 (50 mL) and brine (50 mL). Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to obtain the desired intermediate as a clear oil that solidifies on standing (0.35 g, 20%).

Workup

  1. washwash sequentially with water (3×50 mL), saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
  2. dry with materialDry the organic phase over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-87c897f4081144dab8f8ddf333d8f5b6
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…