Sulfuric Acid → HCID 69241779, compound

HRID 1591518Notes

Reaction equation

HRID 1591518 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([CH:9]=[CH:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[N:3]=1.S(=O)(=O)(O)O.[NH:24]1[C:31](=[O:32])[CH2:30][C:28](=[O:29])[NH:27][C:25]1=[O:26]>C(O)CCCC>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([CH:9]=[CH:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[C:30]3[C:28](=[O:29])[NH:27][C:25](=[O:26])[NH:24][C:31]3=[O:32])=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6211Barbituric AcidHCID 72554651HCID 72554651, compound

Product 1

HCID 69241779HCID 69241779, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
140 °C

Procedure

To 7.29 g (30 mmol) of 4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]-benzaldehyde suspended in 150 mL of 1-pentanol at 130° C. was cautiously added 75 mL of hot aqueous sulfuric acid (25 mL of concentrated sulfuric acid was added to 50 mL of water with cautious while stirring). The solid dissolved immediately, and a yellow solution was obtained. To this solution, 4.61 g (36 mmol) of powdered barbituric acid was added while stirring vigorously at 140° C. Yellow precipitate appeared immediately. The mixture was slightly refluxed at 140° C. for 10 min then filtrated while it was hot. Solid washed with 50 mL of warm 1-pentanol, then suspended in 300 mL of water and neutralized with saturated aqueous NaHCO3. The solid was collected by filtration and washed with water. Yield: 9.72 g of yellow product. Yield=88%. 1HNMR (400 MHz, DMSO): δ11.519 (s, 1H), 11.375 (s, 1H), 8.378 (s, 1H), 8.234 (d, J=8.0 Hz, 2H), 7.915 (d, J=16.0 Hz, 1H), 7.857 (d, J=8.0 Hz, 2H), 7.101 (br, 4H), 7.047 (d, J=16.0 Hz, 1H). m.p.>350° C. EA found: C, 52.20; H, 3.86; N, 26.12. Calculated for C16H13N7O3.H2O: C, 52.03; H, 4.09; N, 26.55. MS (rel. abundance): M++1 (68), M++2 (13), 242.1 (5), 217.1 (6), 179.0 (15), 157.0 (30), 101.0 (55), 79.1 (100). MS (high resolution, ES+): MH+(352.1158).

Workup

  1. dissolutionThe solid dissolved immediately
  2. customa yellow solution was obtained
  3. temperatureThe mixture was slightly refluxed at 140° C. for 10 min
  4. filtrationthen filtrated while it
  5. washSolid washed with 50 mL of warm 1-pentanol
  6. filtrationThe solid was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-a040c71b7e7447ce82f8d2623bce5672
Source dataset
uspto-grants-2007_11
Patent number
US07291293B2

Reaction notes

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