Barbituric Acid → HCID 18455553, compound

HRID 1820646Notes

Reaction equation

HRID 1820646 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH:16]([CH3:18])[O:15][CH:14]([CH3:19])[CH2:13]2)=[C:8]([CH:11]=1)[CH:9]=O)(=[O:3])[CH3:2].[NH:20]1[C:27](=[O:28])[CH2:26][C:24](=[O:25])[NH:23][C:21]1=[O:22]>C(O)(C)C>[C:1]([C:4]1[CH:11]=[C:8]2[C:7](=[CH:6][CH:5]=1)[N:12]1[CH2:17][CH:16]([CH3:18])[O:15][CH:14]([CH3:19])[CH:13]1[C:26]1([C:24](=[O:25])[NH:23][C:21](=[O:22])[NH:20][C:27]1=[O:28])[CH2:9]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 18455601HCID 18455601, compound

Product 1

HCID 18455553HCID 18455553, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-Acetyl-2-(2,6-dimethylmorpholin-4-yl)benzaldehyde (from Step 3, 0.34 g, 1.3 mmol) and barbituric acid (0.175 g, 1.36 mmol) are dissolved in isopropanol (6 ml) and heated at reflux for 1 hour. The cooled reaction mixture is stored at 0° C. overnight. The light yellow solid is isolated by filtration, washed with cold isopropanol and dried in a vacuum oven (20 Torr, 90° C.) for 2 days to afford 0.48 g (100%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.8, 11.45, 7.70, 7.52, 6.92, 4.36, 4.21, 3.82, 3.76, 3.60, 3.53, 3.43, 2.90, 2.40, 1.15, 0.92.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customThe cooled reaction mixture
  4. customThe light yellow solid is isolated by filtration
  5. washwashed with cold isopropanol
  6. customdried in a vacuum oven (20 Torr, 90° C.) for 2 days

Sources & evidence

ORD record
ord-1734a8f1dc6c492d9b90336f753852a7
Source dataset
uspto-grants-2009_10
Patent number
US07605157B2

Reaction notes

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