2-Butyn-1-ol → HCID 58610431, compound

HRID 1594412Notes

Reaction equation

HRID 1594412 reaction equation
CS([C:5]1[N:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH2:11]2)[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:13]1[CH2:14][CH2:15][CH:10]([C:8]2[S:7][N:6]=[C:5]([O:21][CH2:17][C:18]#[C:19][CH3:20])[N:9]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 69027278HCID 69027278, compound

Product 1

HCID 58610431HCID 58610431, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

400 mg of 3-methylsulfonyl-5-(4-methylcyclohexyl)-1,2,4-thiadiazole and 129 mg of 2-butyn-1-ol were dissolved in 3 ml of N,N-dimethylformamide, 80 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 258 mg of 5-(4-methylcyclohexyl)-3-(2-butynyloxy)-1,2,4-thiadiazole (hereinafter referred to as the present invention compound (12)).

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-3255b1adb4744e6296c2bf26876e6e84
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

Loading…