Ethanol → HCID 23070678, compound

HRID 501451Notes

Reaction equation

HRID 501451 reaction equation
[NH4+]=[S:2].C(O)C.[CH2:6]([N:10]1[C:14]([C:15]#[N:16])=[C:13]([CH2:17][OH:18])[N:12]=[C:11]1[N:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)[C:7]#[C:8][CH3:9]>C(OCC)(=O)C>[CH2:6]([N:10]1[C:14]([C:15](=[S:2])[NH2:16])=[C:13]([CH2:17][OH:18])[N:12]=[C:11]1[N:19]1[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]1)[C:7]#[C:8][CH3:9]

Participants

4

Reactant 2

HCID 702EthanolHCID 23070798HCID 23070798, compound

Product 1

HCID 23070678HCID 23070678, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10 ml of a 50% aqueous solution of ammonium sulfide was added to a 50 ml ethanol solution of 3.596 g of t-butyl 4-[1-(2-butynyl)-5-cyano-4-hydroxymethyl-1H-imidazol-2-yl]piperazine-1-carboxylate, and the mixture was stirred at room temperature for 16 hours. 400 ml of ethyl acetate was added to the solution, and the mixture was washed three times with 100 ml of water and then with 100 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 3.221 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (4:1).

Workup

  1. washthe mixture was washed three times with 100 ml of water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd10370680974288b263e0b921b384bf
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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