Water → HCID 72554651, compound

HRID 1591517Notes

Reaction equation

HRID 1591517 reaction equation
[C:1]1([CH:9]=O)[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.O.[CH3:17][C:18]1[N:23]=[C:22]([NH2:24])[N:21]=[C:20]([NH2:25])[N:19]=1>CO>[NH2:25][C:20]1[N:21]=[C:22]([NH2:24])[N:23]=[C:18]([CH:17]=[CH:9][C:1]2[CH:2]=[CH:3][C:4]([CH:7]=[O:8])=[CH:5][CH:6]=2)[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 10949AcetoguanamineHCID 12173Terephthalaldehyde

Product 1

HCID 72554651HCID 72554651, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To 107.2 g (800 mmol) of benzene-1,4-dicarboxaldehyde suspended in 450 mL methanol was added with stirring 294.0 g of 31% aqueous sulfuric acid (50 mL of concentrated sulfuric acid was added slowly to 200 mL of water while stirring). The solid dissolved and a yellow solution was obtained. The solution was heated to 80° C. with an oil bath, and 25.0 g (200 mmol) 6-methyl-[1,3,5]triazine-2,4-diamine powder was added. The solution was stirred at 80° C. for 8 h then cooled to room temperature. Next, 1.2 g of yellow byproduct (1,4-bis[4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]]-benzene) was removed by filtration, and the filtrate was treated with 2000 mL water. The resulting solid was collected by filtration and washed with saturated aqueous NaHCO3 and water until neutral. The excess benzene-1,4-dicarboxaldehyde was removed by sonicating and washing with acetone three times. Yield: 20.0 g of light yellow product. Yield=41%. 1HNMR (500 MHz, DMSO): δ9.992 (s, 1H), 7.894 (d, J=8.0 Hz, 2H), 7.847 (d, J=7.5 Hz, 2H), 7.806 (d, J=15.5 Hz, 1H), 6.928 (d, J=15.5 Hz, 1H), 6.806 (br, 4H). 13CNMR (500 MHz, DMSO): δ 193.914, 193.417, 170.671, 167.847, 141.836, 136.833, 131.461, 130.688, 128.883.

Workup

  1. additionwas added
  2. dissolutionThe solid dissolved
  3. customa yellow solution was obtained
  4. stirringThe solution was stirred at 80° C. for 8 h
  5. temperaturethen cooled to room temperature
  6. customNext, 1.2 g of yellow byproduct (1,4-bis[4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]]-benzene) was removed by filtration
  7. additionthe filtrate was treated with 2000 mL water
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with saturated aqueous NaHCO3 and water until neutral
  10. customThe excess benzene-1,4-dicarboxaldehyde was removed
  11. customby sonicating
  12. washwashing with acetone three times

Sources & evidence

ORD record
ord-0c1cb86547d14816b5900813487badbf
Source dataset
uspto-grants-2007_11
Patent number
US07291293B2

Reaction notes

Loading…