Sodium hydride → HCID 23032438, compound

HRID 917328Notes

Reaction equation

HRID 917328 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.Cl[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[CH2:16][OH:17].[H-].[Na+].[Cl-:20].[NH4+]>CN(C)C=O>[Cl:20][C:14]1[N:13]=[CH:12][C:11]([CH2:16][O:17][C:2]2[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=2)=[CH:10][CH:15]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 435084(4-chloropyridin-3-yl)methanolHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 23032438HCID 23032438, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 2.5 ml of N,N-dimethylformamide were dissolved 200 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 207 mg of 4-chloro-3-pyridylmethyl alcohol, 59 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 hour 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 170 mg of 5-(6-chloro-3-pyridyl)methyloxy-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (21)).

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-0b1aaad3cfae4c308a0e5776dc373fcc
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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