2-Butyn-1-ol → HCID 58610440, compound

HRID 1594408Notes

Reaction equation

HRID 1594408 reaction equation
CS([C:5]1[N:9]=[C:8]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[S:7][N:6]=1)(=O)=O.[CH2:15]([OH:19])[C:16]#[C:17][CH3:18].[H-].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[CH:10]1([C:8]2[S:7][N:6]=[C:5]([O:19][CH2:15][C:16]#[C:17][CH3:18])[N:9]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 69025990HCID 69025990, compound

Product 1

HCID 58610440HCID 58610440, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

300 mg of 3-methylsulfonyl-5-cyclopentyl-1,2,4-thiadiazole and 99 mg of 2-butyn-1-ol were dissolved in 3 g of N,N-dimethylformamide, 62 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 30 minutes under ice-cooling. Then, the reaction mixture was added to saturated brine, and extracted with t-butyl methyl ether. The organic layer was concentrated under reduced pressure, and the residue obtained was subjected to silica gel column chromatography to give 155 mg of 5-cyclopentyl-3-(2-butynyloxy)-1,2,4-thiadiazole (hereinafter referred to as the present invention compound (3)).

Workup

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

Sources & evidence

ORD record
ord-1762096a1d564bb9929e0fe6fe3ba9c6
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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