Sodium methanethiolate → 5-Methyl-6-(methylthio)nicotinonitrile

HRID 368286Notes

Reaction equation

HRID 368286 reaction equation
[CH3:1][S-:2].[Na+].F[C:5]1[N:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:6]=1[CH3:13].CCOC(C)=O.CCCCCC>CC(O)C.O>[CH3:13][C:6]1[CH:7]=[C:8]([C:11]#[N:12])[CH:9]=[N:10][C:5]=1[S:2][CH3:1]

Participants

6

Reactant 3

HCID 4378561Sodium methanethiolateHCID 21226206Ethyl acetate hexaneHCID 232882695-Cyano-2-fluoro-3-picoline

Product 1

HCID 232882705-Methyl-6-(methylthio)nicotinonitrileYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

To a stirred suspension of sodium thiomethoxide (1.66 g, 23.71 mmol) in 2-propanol (20 mL) at room temperature under a nitrogen atmosphere was added a suspension of 6-fluoro-5-methyl-3-pyridinecarbonitrile (2.69 g, 19.76 mmol) in 2-propanol (10 mL). After one hour stirring at room temperature, TLC (25% EtOAc/hexane) indicated loss of starting material. The reaction mixture was diluted with water (20 mL) and filtered. The filtrate was extracted twice with ether (25 mL×2). The organic layers were combined, washed with water and evaporated in vacuo to give the desired product (2.57 g, 79.1%) as yellow fluffy crystals.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. extractionThe filtrate was extracted twice with ether (25 mL×2)
  4. washwashed with water
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ecd1601fdec84cb687be0fe00dcf6a94
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

Loading…