Sodium hydride → HCID 18942616, compound

HRID 355481Notes

Reaction equation

HRID 355481 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:11](=[O:12])[CH2:10][C:8](=[O:9])[N:7]([CH3:13])[C:5]1=[O:6].Br[CH2:15][C:16](=[CH2:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(#N)C>[CH2:20]([O:19][C:17]([C:16](=[CH2:22])[CH2:15][C:10]1([CH2:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH2:15])[C:11](=[O:12])[N:4]([CH3:3])[C:5](=[O:6])[N:7]([CH3:13])[C:8]1=[O:9])=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69860Dimethylbarbituric acidHCID 3106202-(Bromomethyl)acrylic acid ethyl ester

Product 1

HCID 18942616HCID 18942616, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of sodium hydride (0.75 g, 80% dispersion in oil) and 1,3-dimethylbarbituric acid (1.56 g, 0.01 mol) in acetonitrile (10 mL) was added a solution of ethyl 2-(bromomethyl)propenoate (3.86 g, 0.02 mol) in acetonitrile (5 mL). The resulting mixture was allowed to stir at room temperature under nitrogen overnight. Thin layer chromatography (ethyl acetate/petroleum spirit: 1/4) indicated all the starting materials had been consumed. Water (30 mL) was added and the slightly pink solution was extracted three times with ethyl acetate (3×30 mL). The combined organic layer was washed with water, brine and then dried over anhydrous magnesium sulfate. After removal of solvent, purification by column chromatography (silica-gel 100 g, ethyl acetate:pet. spirit 40°-60° C. 1:4) gave pure product (11) (3.20 g, 84%) as a colourless liquid which solidified when stored in the freezer. 1 H-NMR (CDCl3) δ(ppm): 1.22 (t, 6H); 3.00 (s, 4H); 3.20 (s, 6H); 4.08 (q, 4H); 5.50 (s, 2H) and 6.15 (s, 2H). 13C-NMR (CDCl3) δ(ppm): 13.9, 28.2, 39.9, 55.4, 61.0, 128.2, 135.2, 151.0, 166.2 and 169.9.

Workup

  1. customhad been consumed
  2. additionWater (30 mL) was added
  3. extractionthe slightly pink solution was extracted three times with ethyl acetate (3×30 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of solvent, purification by column chromatography (silica-gel 100 g, ethyl acetate:pet. spirit 40°-60° C. 1:4)

Sources & evidence

ORD record
ord-1ba071c6f43d4db5bc9e7130b782749f
Source dataset
uspto-grants-1998_11
Patent number
US05830966

Reaction notes

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