Barbituric Acid → HCID 10001155, compound

HRID 1820648Notes

Reaction equation

HRID 1820648 reaction equation
[CH2:1]([C@H:3]1[O:8][C@@H:7]([CH2:9][CH3:10])[CH2:6][N:5]([C:11]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:12]=2[CH:13]=O)[CH2:4]1)[CH3:2].[NH:22]1[C:29](=[O:30])[CH2:28][C:26](=[O:27])[NH:25][C:23]1=[O:24]>CO>[CH2:9]([C@H:7]1[O:8][C@@H:3]([CH2:1][CH3:2])[C@@H:4]2[C:28]3([CH2:13][C:12]4[C:11]([N:5]2[CH2:6]1)=[CH:18][CH:17]=[C:16]([N+:19]([O-:21])=[O:20])[CH:15]=4)[C:26](=[O:27])[NH:25][C:23](=[O:24])[NH:22][C:29]3=[O:30])[CH3:10]

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 58847236HCID 58847236, compound

Product 1

HCID 10001155HCID 10001155, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

2-(cis-2,6-Diethylmorpholin-4-yl)-5-nitrobenzaldehyde (1.58 g, 5.39 mmol) is combined with barbituric acid (767 mg, 5.39 mmol, Aldrich) in a flask with MeOH (17 mL). The sealed reaction is stirred with heating at 80° C. overnight. The solvent is removed by rotary evaporation and the product is purified on a Biotage Flash 40M+ using a 10% MTBE in CH2Cl2 as eluent. The product is dried under vacuum and recrystallized from CH3OH/heptane. The large crystals are crushed and dried under vacuum @100° C. yielding 1.04 g (48%) of bright yellow crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.86, 0.97, 1.08, 1.24, 1.45, 1.58, 2.84, 3.03, 3.34, 3.60, 3.97, 4.26, 7.01, 7.84, 7.98, 11.56, 11.87.

Workup

  1. customThe sealed reaction
  2. customThe solvent is removed by rotary evaporation
  3. customthe product is purified on a Biotage Flash 40M+
  4. customThe product is dried under vacuum
  5. customrecrystallized from CH3OH/heptane
  6. customThe large crystals are crushed
  7. customdried under vacuum @100° C.

Sources & evidence

ORD record
ord-c6df7431ec0a400796e9282940726125
Source dataset
uspto-grants-2009_10
Patent number
US07605157B2

Reaction notes

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