Hydrochloric Acid → HCID 58495647, compound

HRID 1191055Notes

Reaction equation

HRID 1191055 reaction equation
[Na].[CH:2]1([SH:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.Cl>C(O)C>[CH:2]1([S:8][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 145174-FluorobenzonitrileHCID 15290CyclohexanethiolHCID 5360545Sodium

Product 1

HCID 58495647HCID 58495647, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve sodium metal (343 mg, 14.9 mmoles) in anhydrous ethanol (20 mL) at room temperature under nitrogen atmosphere. Then add cyclohexyl mercaptan (2 mL, 16.37 mmoles) and stir at room temperature for 30 min. Add then neat 4-fluoro-benzonitrile (1.8 g, 14.9 mmol) and heat the resulting solution at 80° C. overnight. Cool the reaction to room temperature and quench the reaction by adding 1N aqueous HCl (100 mL). Concentrate the mixture in vacuo and take up the residue with EtOAc (100 mL). Wash the organic layer with saturated aqueous NaHCO3 (100 mL) and brine (100 mL). Dry the organic phase over MgSO4 and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g, pre-packed cartridge) eluting with cyclohexane/EtOAc (98:2 to 80:20 gradient) to afford the desired intermediate (2.2 g, 68%). GC-MS m/z: 217 (M+).

Workup

  1. additionAdd
  2. temperatureCool
  3. customthe reaction to room temperature
  4. customquench
  5. customthe reaction
  6. concentrationConcentrate the mixture in vacuo
  7. washWash the organic layer with saturated aqueous NaHCO3 (100 mL) and brine (100 mL)
  8. dry with materialDry the organic phase over MgSO4
  9. concentrationconcentrate in vacuo
  10. customPurify the crude mixture by chromatography on silica gel (120 g, pre-packed cartridge)
  11. washeluting with cyclohexane/EtOAc (98:2 to 80:20 gradient)

Sources & evidence

ORD record
ord-8a4c2a9e2c524212ad60e333a1b5c09c
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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