2-Butyn-1-ol → HCID 58792114, compound

HRID 2222134Notes

Reaction equation

HRID 2222134 reaction equation
CS([C:5]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)[S:7][N:6]=1)(=O)=O.[CH2:16]([OH:20])[C:17]#[C:18][CH3:19].[H-].[Na+]>O1CCCC1>[CH2:16]([O:20][C:5]1[N:9]=[C:8]([N:10]2[CH2:11][CH2:12][S:13][CH2:14][CH2:15]2)[S:7][N:6]=1)[C:17]#[C:18][CH3:19]

Participants

5

Reactant 3

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 69219894HCID 69219894, compound

Product 1

HCID 58792114HCID 58792114, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 3 ml of tetrahydrofuran were dissolved 398 mg of 3-methylsulfonyl-5-(thiomorpholino)-1,2,4-thiadiazole and 180 mg of 2-butyn-1-ol, and 102 mg of sodium hydride (oil suspension; content: 60 weight %) was added at room temperature. The mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated. The residue was subjected to recrystallization from a mixed solvent of hexane-ethyl acetate to obtain 246 mg of 3-(2-butynyloxy)-5-thiomorpholino-1,2,4-thiadiazole (hereinafter, referred to as the present compound (23)).

Workup

  1. additionwas added at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customThe residue was subjected to recrystallization from a mixed solvent of hexane-ethyl acetate

Sources & evidence

ORD record
ord-0d0daf32e39e4ba4b4afec08db50e435
Source dataset
uspto-grants-2008_05
Patent number
US07371746B2

Reaction notes

Loading…