2-Amino-4-chlorobenzoic acid → HCID 13525068, compound

HRID 1981583Notes

Reaction equation

HRID 1981583 reaction equation
[CH3:1][N:2]1[C:9]([NH2:10])=[C:8]([NH2:11])[C:6](=[O:7])[N:5]([CH3:12])[C:3]1=[O:4].[NH2:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[C:16](O)=O>CO>[NH2:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[C:16]1[NH:11][C:8]2[C:6](=[O:7])[N:5]([CH3:12])[C:3](=[O:4])[N:2]([CH3:1])[C:9]=2[N:10]=1

Participants

4

Reactant 2

HCID 666462-Amino-4-chlorobenzoic acidHCID 795015,6-Diamino-1,3-dimethyluracil

Product 1

HCID 13525068HCID 13525068, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,3-dimethyl-5,6-diaminouracil (0.01 mol) was suspended in 50 ml methanol. 2-amino-4-chlorobenzoic acid (0.01 mol) was added, followed by 0.01 mol of DICD. The reactants were stirred at room temperature for 15 min, then filtered and washed with methanol. The solid was boiled in 40 ml 2.5N NaOH for five min, filtered hot, and the eluate was left to cool for three hours. The material which precipitated on cooling was filtered without washing, redissolved in 40 ml water, and precipitated by neutralization with concentrated HCl. The solid was collected by filtration, washed with H2O, and dried. The product was purified by suspending in 100 ml water, adding NaOH until the compound was dissolved, filtering, precipitating the solid with HCl, filtering, washing with H2O, and drying. The product was identified by chemical ionization mass spectrometry and elemental analysis. Yield 12.5%.

Workup

  1. filtrationfiltered
  2. washwashed with methanol
  3. waitThe solid was boiled in 40 ml 2.5N NaOH for five min
  4. filtrationfiltered hot
  5. waitthe eluate was left
  6. temperatureto cool for three hours
  7. customThe material which precipitated
  8. temperatureon cooling
  9. filtrationwas filtered
  10. washwithout washing
  11. dissolutionredissolved in 40 ml water
  12. customprecipitated by neutralization with concentrated HCl
  13. filtrationThe solid was collected by filtration
  14. washwashed with H2O
  15. customdried
  16. customThe product was purified
  17. additionadding NaOH until the compound
  18. dissolutionwas dissolved
  19. filtrationfiltering
  20. customprecipitating the solid with HCl
  21. filtrationfiltering
  22. washwashing with H2O
  23. customdrying

Sources & evidence

ORD record
ord-b6a91738b88a4731a9d97320e99aba9b
Source dataset
uspto-grants-1986_06
Patent number
US04593095

Reaction notes

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