Potassium Hydroxide → HCID 58495683, compound

HRID 1190954Notes

Reaction equation

HRID 1190954 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[OH-].[K+].[CH:12]1([SH:17])[CH2:16][CH2:15][CH2:14][CH2:13]1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:17][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 15510CyclopentanethiolHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 58495683HCID 58495683, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Slurry 2-chloro-5-chloromethyl-pyridine (8.1 g, 45 mmol) and potassium hydroxide (10.3 g, 225 mmol) in methanol at 0° C. under nitrogen atmosphere. Add cyclopentyl mercaptan (4.8 mL, 45 mmol), warm the mixture to room temperature and stir for 16 h. Concentrate in vacuo and partition the residue between water (50 mL) and DCM (200 mL). Collect the organic phase, concentrate in vacuo and purify the crude mixture by chromatography on silica gel (330 g) eluting with hexane/EtOAc (49:1 to 4:1 gradient) to obtain the desired intermediate as an oil (8.4 g, 82%). MS (APCI+) m/z: 227 (M)+.

Workup

  1. customat 0° C.
  2. concentrationConcentrate in vacuo
  3. custompartition the residue between water (50 mL) and DCM (200 mL)
  4. customCollect the organic phase
  5. concentrationconcentrate in vacuo
  6. custompurify the crude mixture by chromatography on silica gel (330 g)
  7. washeluting with hexane/EtOAc (49:1 to 4:1 gradient)

Sources & evidence

ORD record
ord-e91cdffa4c3d44e894ac26d399d45091
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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