Sodium hydride → HCID 178512078, compound

HRID 1613282Notes

Reaction equation

HRID 1613282 reaction equation
[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][NH:5]1)#[N:2].[H-].[Na+].Cl[CH2:12][C:13]#[C:14][CH2:15][NH:16][C:17](=[O:32])[C:18]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CS(C)=O>[C:1]([N:3]=[C:4]1[NH:8][CH2:7][CH2:6][N:5]1[CH2:12][C:13]#[C:14][CH2:15][NH:16][C:17](=[O:32])[C:18]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)([OH:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15023451N-(4-chloro-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamideHCID 178512073HCID 178512073, compound

Product 1

HCID 178512078HCID 178512078, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(cyanoimino)imidazolidine (0.28 g) in dimethyl sulfoxide (10 ml}was added 60% sodium hydride dispersed in mineral oil (0.1 g) and the mixture was stirred at room temperature for 25 minutes. After an addition of N-(4-chloro-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide (0.40 g), the mixture was stirred at the same temperature for further 45 minutes and then quenched with cold water (50 ml). The mixture was extracted with ethyl acetate (50 ml×3). The combined extracts were washed with sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (20:1) as an eluent to give N-[4-{2-(cyanoimino)-1-imidazolidinyl}-2-butynyl]-2-cyclohexyl-2-hydroxy-2-phenylacetamide (0.37 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for further 45 minutes
  2. customquenched with cold water (50 ml)
  3. extractionThe mixture was extracted with ethyl acetate (50 ml×3)
  4. washThe combined extracts were washed with sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (20:1) as an eluent

Sources & evidence

ORD record
ord-7868f56b933b4a8db06023a99b3c9051
Source dataset
uspto-grants-1993_03
Patent number
US05192779

Reaction notes

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