3-Pyridinemethanol → HCID 23032463, compound

HRID 917327Notes

Reaction equation

HRID 917327 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]O)[CH:10]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:2]2[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 23032463HCID 23032463, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 2 ml of N,N-dimethylformamide were dissolved 100 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 78 mg of 3-pyridinemethanol, 78 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 0.5 hour under ice-cooling and for 1 hours at room temperature. The reaction mixture was added to saturated ammonium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 88 mg of 5-(3-pyridylmethyl)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (20)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. extractionextracted with t-butyl methyl ether
  4. concentrationThe organic layer was concentrated
  5. customthe residue obtained

Sources & evidence

ORD record
ord-b594c35055bc4a809cb0f85bf1d9726c
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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