2-Butyn-1-ol → 5-(2-Methylcyclohexyl)-3-(2-butynyloxy)-1,2,4-thiadiazole

HRID 1594411Notes

Reaction equation

HRID 1594411 reaction equation
CS([C:5]1[N:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])[S:7][N:6]=1)(=O)=O.[CH2:17]([OH:21])[C:18]#[C:19][CH3:20].[H-].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[CH3:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[C:8]1[S:7][N:6]=[C:5]([O:21][CH2:17][C:18]#[C:19][CH3:20])[N:9]=1

Participants

6

Reactant 3

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 690272813-Methylsulfonyl-5-(2-methylcyclohexyl)-1,2,4-thiadiazole

Product 1

HCID 586104275-(2-Methylcyclohexyl)-3-(2-butynyloxy)-1,2,4-thiadiazoleYield 25.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

160 mg of 3-methylsulfonyl-5-(2-methylcyclohexyl)-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 at 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 39 mg of 5-(2-methylcyclohexyl)-3-(2-butynyloxy)-1,2,4-thiadiazole (hereinafter referred to as the present invention compound (10)).

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-27ae461b21984694bb6106400290a3f4
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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