Thiophenol → HCID 178507299, compound

HRID 128927Notes

Reaction equation

HRID 128927 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH2:9])[CH:5]=[C:4](Cl)[N:3]=1.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=CC=1.C(N(CC)CC)C>C(O)CC>[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH2:9])[CH:5]=[C:4]([C:14]2[S:17][CH:11]=[CH:16][CH:15]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 178507684HCID 178507684, compound

Product 1

HCID 178507299HCID 178507299, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

5 g of 2,4-diamino-6-chloropyrimidine 3-oxide, 6.85 g of thiophenol and 11.5 g of triethylamine are placed in 110 ml of n-propanol. The reaction mixture is heated at reflux for 24 hours. It is evaporated to dryness. The residue is taken up in 25 ml of ethyl ether, stirred for 1/2 an hour, filtered on sintered glass and rinsed with 2×25 ml of ethyl ether. The precipitate is taken up in 75 ml of water. The pH is adjusted to 1 with concentrated hydrochloric acid. After stirring for 1/2 an hour, the pH is returned to 8 by addition of concentrated sodium hydroxide solution. The precipitate is filtered, rinsed with 10 ml of water and then recrystallized twice from a 75/25 ethanol/water mixture. 3.35 g of 2,4-diamino-6-thiophenylpyrimidine 3-oxide are obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 24 hours
  3. customIt is evaporated to dryness
  4. filtrationfiltered on sintered glass
  5. washrinsed with 2×25 ml of ethyl ether
  6. stirringAfter stirring for 1/2 an hour
  7. additionthe pH is returned to 8 by addition of concentrated sodium hydroxide solution
  8. filtrationThe precipitate is filtered
  9. washrinsed with 10 ml of water
  10. customrecrystallized twice from a 75/25 ethanol/water mixture

Sources & evidence

ORD record
ord-fa64921b3692415da45c1ea466002c11
Source dataset
uspto-grants-1995_11
Patent number
US05466694

Reaction notes

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