Butanedione → 1H-Imidazole-4-methanol, 5-methyl-2-phenyl-

HRID 1863361Notes

Reaction equation

HRID 1863361 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:11][C:12](=O)[C:13](=O)[CH3:14].[OH-:17].[Na+]>O>[CH3:11][C:12]1[NH:10][C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:9][C:13]=1[CH2:14][OH:17]

Participants

5

Reactant 3

HCID 650ButanedioneHCID 14798Sodium Hydroxide2×HCID 80289Benzamidine, hydrochloride

Product 1

HCID 836581H-Imidazole-4-methanol, 5-methyl-2-phenyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 100 gm. portion of benzamidine hydrochloride is dissolved in a minimum of water (350 ml.) at room temperature. A 67 gm. portion of freshly distilled 2,3-butanedione is added giving a yellow solution. Adjusting the pH to 6-7 with 2N NaOH gives a solid which is allowed to stand at 0° C. for 2 hours, collected, pressed dry and then washed with 100 ml. of acetone. This material is heated with stirring on a steam bath with 855 ml. of concentrated HCl and 2437 ml. of water for 4 hours giving a solution. Cooling to room temperature overnight and then to 0° C. produces a solid which is collected and air dried. This solid is dissolved in 350 ml. of ethanol, filtered and cooled producing a gel, which is taken up in 250 ml. of 50°-60° C. water, adjusted to pH 5.5 with concentrated NaOH and then to pH 7-8 with solid KHCO3. The mixture is cooled to 0° C. and the product is collected, washed with water, and air dried. This product is recrystallized from one liter of methanol giving the final product, m.p. 197°- 199° C.

Workup

  1. customgiving a yellow solution
  2. customgives a solid which
  3. customcollected
  4. custompressed dry
  5. washwashed with 100 ml
  6. temperatureThis material is heated
  7. customof water for 4 hours giving a solution
  8. customto 0° C. produces a solid which
  9. customis collected
  10. customair dried
  11. dissolutionThis solid is dissolved in 350 ml
  12. filtrationof ethanol, filtered
  13. temperaturecooled
  14. customproducing a gel, which
  15. customof 50°-60° C.
  16. temperatureThe mixture is cooled to 0° C.
  17. customthe product is collected
  18. washwashed with water, and air
  19. customdried
  20. customThis product is recrystallized from one liter of methanol giving the final product, m.p. 197°- 199° C.

Sources & evidence

ORD record
ord-827e5be99d4848b7a73e9889c9b3379e
Source dataset
uspto-grants-1979_09
Patent number
US04168964

Reaction notes

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