Propyl mercaptan → HCID 58671590, compound

HRID 1811569Notes

Reaction equation

HRID 1811569 reaction equation
F[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.[CH2:10]([SH:13])[CH2:11][CH3:12].[OH-].[K+]>CCO>[CH3:8][C:6]1[C:5]([NH2:9])=[CH:4][CH:3]=[C:2]([S:13][CH2:10][CH2:11][CH3:12])[N:7]=1

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 14797Potassium HydroxideHCID 247292406-Fluoro-2-methylpyridin-3-amine

Product 1

HCID 58671590HCID 58671590, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-fluoro-2-methyl-pyridin-3-ylamine (2.01 g, 16 mmol), propane-1-thiol (3.0 mL, 33 mmol), and potassium hydroxide (1.8 g, 32 mmol) in 3 mL EtOH were heated under microwave irradiation at 100° C. for 1 h and then at 150° C. for 2 h. Mixture was extracted with CH2Cl2 and brine. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by column chromatography (hexane/AcOEt 2:1) to give 2-methyl-6-propylsulfanyl-pyridin-3-ylamine (2.18 g, 75% yield) as a colorless oil. 1HNMR (CDCl3, 400 MHz) δ 0.99-1.03 (t, J=7.3 Hz, 3H), 1.64-1.73 (m, 2H), 2.39 (s, 3H), 3.02-3.05 (t, J=7.3 Hz, 2H), 3.48 (s, 2H), 6.82-6.84 (d, J=8.2 Hz, 1H), 6.93-6.95 (d, J=8.2 Hz, 1H). Exact mass calculated for C9H14N2S 182.09 found 183.0 (MH+).

Workup

  1. extractionMixture was extracted with CH2Cl2 and brine
  2. dry with materialOrganic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customResidue was purified by column chromatography (hexane/AcOEt 2:1)

Sources & evidence

ORD record
ord-d2583835079a4e14aac455454454b2c7
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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