Dimethyl Carbonate → HCID 123593308, compound

HRID 1467829Notes

Reaction equation

HRID 1467829 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([N:5]([CH3:15])[C:6](=[O:14])[N:7]([CH3:13])[C:8]2=[O:12])=[N:3]1.[H-].[Na+].[CH3:18][O:19][C:20](=O)[O:21]C>>[CH3:1][N:2]1[C:10]([CH2:11][C:20]([O:19][CH3:18])=[O:21])=[C:9]2[C:4]([N:5]([CH3:15])[C:6](=[O:14])[N:7]([CH3:13])[C:8]2=[O:12])=[N:3]1

Participants

4

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 53675961HCID 53675961, compound

Product 1

HCID 123593308HCID 123593308, compound

Procedure

To a stirred solution of Step 5 intermediate (3.8 g, 18.24 mmol) in dimethylcarbonate (91 ml) was added sodium hydride (60% dispersion in mineral oil, 4.5 g, 187.5 mmol) at room temperature. The reaction mixture was heated to reflux for overnight. The reaction mixture was cooled to room temperature, quenched into 1N HCl (200 ml), extracted with ethyl acetate (2×250 ml) and the combined organic layers were washed with water (2×250 ml), dried over Na2SO4 and concentrated. The residue obtained was triturated in hexane, solid obtained was filtered to give 5.5 g of the product as a white solid; 1H NMR (300 MHz, DMSO-d6): δ 3.37 (s, 3H), 3.50 (s, 3H), 3.82 (s, 5H), 3.90 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for overnight
  3. customquenched into 1N HCl (200 ml)
  4. extractionextracted with ethyl acetate (2×250 ml)
  5. washthe combined organic layers were washed with water (2×250 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customwas triturated in hexane
  10. customsolid obtained
  11. filtrationwas filtered

Sources & evidence

ORD record
ord-ae7ffd90597140de9b9761a822958daa
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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