Sulfuric Acid → HCID 59484956, compound

HRID 925491Notes

Reaction equation

HRID 925491 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:15]=[CH:14][C:13](N=CN(C)C)=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:22]>O>[OH:22][C:13]1[CH:12]=[N:11][C:10]([C:6]2[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][CH:7]=2)=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59484960HCID 59484960, compound

Product 1

HCID 59484956HCID 59484956, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

5.10 g of N′-[2-(3-acetylphenyl)pyrimidin-5-yl]-N,N-dimethylformamidine (19 mmol) are suspended in 65 ml of water in a 250 ml one-necked flask provided with magnetic stirrer and condenser, 8.44 ml of 95-97% sulfuric acid (152 mmol) are added, and the mixture is stirred at a bath temperature of 130° C. for 2 h. The mixture is diluted with ice-water, during which a dark-brown resin deposits. The aqueous solution is decanted off and extracted with dichloromethane. The combined dichloromethane phases are dried, filtered and evaporated to dryness, and the residue is triturated with ether, filtered off with suction and dried (═K1). The deposited dark-brown resin is extracted by stirring with tetrahydrofuran, filtered off with suction, the crystals are discarded, and the mother liquor is evaporated to dryness (═R1). The aqueous phase from the dichloromethane extraction is evaporated to dryness, the residue is extracted by stirring 2× with tetrahydrofuran, and the combined decanted-off solutions are diluted with di-chloromethane, dried, filtered and evaporated to dryness (═R2). R1 and R2 are combined, adsorbed on silica gel and purified by chromatography (silica gel/dichloromethane+0-5% of methanol). The chromatography residue is triturated with ether, filtered off with suction, washed with ether and dried (═K2).

Workup

  1. customprovided with magnetic stirrer and condenser
  2. customThe aqueous solution is decanted off
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined dichloromethane phases are dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customthe residue is triturated with ether
  8. filtrationfiltered off with suction
  9. customdried (═K1)
  10. extractionThe deposited dark-brown resin is extracted
  11. stirringby stirring with tetrahydrofuran
  12. filtrationfiltered off with suction
  13. customthe mother liquor is evaporated to dryness (═R1)
  14. extractionThe aqueous phase from the dichloromethane extraction
  15. customis evaporated to dryness
  16. extractionthe residue is extracted
  17. stirringby stirring 2× with tetrahydrofuran
  18. additionare diluted with di-chloromethane
  19. customdried
  20. filtrationfiltered
  21. customevaporated to dryness (═R2)
  22. custompurified by chromatography (silica gel/dichloromethane+0-5% of methanol)
  23. customThe chromatography residue is triturated with ether
  24. filtrationfiltered off with suction
  25. washwashed with ether
  26. customdried (═K2)

Sources & evidence

ORD record
ord-d180a2b138424c02b22f89044defd33e
Source dataset
uspto-grants-2016_03
Patent number
US09284300B2

Reaction notes

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