Methanol → HCID 57052728, compound

HRID 973998Notes

Reaction equation

HRID 973998 reaction equation
[C:1](C(OC)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:20])[CH2:15][C:16]#[C:17][CH2:18][NH2:19].[OH-:21].[Na+].[CH3:23]O>>[CH3:13][N:14]([CH3:20])[CH2:15][C:16]#[C:17][CH2:18][N:19]([C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:23]=[O:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 84835Methyl phenylglyoxalateHCID 12259565(4-Aminobut-2-yn-1-yl)dimethylamine

Product 1

HCID 57052728HCID 57052728, compound

Procedure

A solution of methyl benzoylformate (0.50 g) and 4-dimethylamino-2-butynylamine (0.38 g) in methanol (5 ml) was refluxed for 3 hours. To the reaction mixture was added 1N aqueous solution of sodium hydroxide and the mixture was extracted with ethyl acetate. The extract was washed with brine, 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-dimethylamino-2-butynyl)benzoylformamide (0.39 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. 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-c5bd2bb00ed74d868d69b5662755d6bd
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

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