2-Butyn-1-ol → HCID 58610438, compound

HRID 1594413Notes

Reaction equation

HRID 1594413 reaction equation
CS([C:5]1[N:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][CH3:17])[CH2:11]2)[S:7][N:6]=1)(=O)=O.[CH2:18]([OH:22])[C:19]#[C:20][CH3:21].[H-].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[CH2:16]([CH:12]1[CH2:13][CH2:14][CH2:15][CH:10]([C:8]2[S:7][N:6]=[C:5]([O:22][CH2:18][C:19]#[C:20][CH3:21])[N:9]=2)[CH2:11]1)[CH3:17]

Participants

6

Reactant 3

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 69028066HCID 69028066, compound

Product 1

HCID 58610438HCID 58610438, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

170 mg of 3-methylsulfonyl-5-(3-ethylcyclohexyl)-1,2,4-thiadiazole and 52 mg of 2-butyn-1-ol were dissolved in 1.5 ml of N,N-dimethylformamide, 32 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 1 hour under ice-cooling and for 12 hours under room temperature. 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 80 mg of 5-(3-ethylcyclohexyl)-3-(2-butynyloxy)-1,2,4-thiadiazole (hereinafter referred to as the present invention compound (14)).

Workup

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

Sources & evidence

ORD record
ord-c5eb5812fc0f47198ce0429ec604a969
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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