Barbituric Acid → HCID 45137913, compound

HRID 1873644Notes

Reaction equation

HRID 1873644 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)[CH:13]=1)=O>CO>[CH3:29][O:28][C:26](=[O:27])[C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]([CH:10]=[C:7]3[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][C:8]3=[O:9])=[CH:13]2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 5082571HCID 5082571, compound

Product 1

HCID 45137913HCID 45137913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of barbituric acid (1.28 g; 0.01 mol) and methyl 4-((3-formyl-1H-indol-1-yl)methyl)benzoate (2.93 g; 0.01 mol) in methanol (50 ml) were stirred at room temperature. After 10 min the reaction mixture became a solid suspension and the color of reaction mixture changed to yellow color solid suspension. The suspension continued to stir at room temperature for 5 hrs. Solid product was separated by filtration and washed several times with cold methanol (3×5 ml). The isolated yellow solid recrystallized from methanol gave (2) as a yellow crystalline product; m.p. >300° C.; 1H NMR (DMSO-d6): δ 3.82 (s, 3H), 5.79 (s, 2H), 7.33-7.36 (m, 2H), 7.40-7.42 (d, 2H), 7.61-7.63 (m, 1H), 7.91-7.93 (m, 1H), 7.94-7.95 (d, 2H), 8.68 (s, 1H), 9.62 (s, 1H), 11.06 (bs, 1H), 11.14 (bs, 1H); 13C NMR (DMSO-d6): δ 49.9, 52.1, 109.2, 110.7, 111.8, 117.8, 122.9, 123.7, 127.4, 129.0, 129.5, 129.6, 136.2, 141.4, 141.7, 142.6, 150.1, 162.8, 164.1, 165.5.

Workup

  1. customa solid suspension and the color of reaction mixture
  2. stirringto stir at room temperature for 5 hrs
  3. customSolid product was separated by filtration
  4. washwashed several times with cold methanol (3×5 ml)
  5. customThe isolated yellow solid recrystallized from methanol

Sources & evidence

ORD record
ord-d6a1b8857a4c4c779817fc5f2d6664a6
Source dataset
uspto-grants-2012_11
Patent number
US08304421B2

Reaction notes

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