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

HRID 1704187Notes

Reaction equation

HRID 1704187 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:15])C.[OH-].[Na+].[C:19](=O)(O)[O-].[K+]>O>[CH3:19][C:11]1[NH:10][C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:9][C:12]=1[CH2:13][OH:15]

Participants

6

Reactant 4

HCID 650ButanedioneHCID 14798Sodium Hydroxide2×HCID 80289Benzamidine, hydrochlorideHCID 516893Potassium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Benzamidine hydrochloride (100 g) is dissolved in a minimum of water (350 ml) at room temperature. Freshly distilled 2,3-butanedione (67 g) is added giving a yellow solution. Adjusting the pH to 6-7 with 2N sodium hydroxide gives a solid which is allowed to stand at 0° C for 2 hours, collected, pressed dry and then washed with acetone (100 ml). This material is heated with stirring on a steam bath with concentrated hydrochloric acid (855 ml) and water (2437 ml) 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 ethanol (350 ml), 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 sodium hydroxide and then to pH 7-8 with solid potassium bicarbonate. The mixture is cooled to 0° C and the product is collected, washed with water, and air dried. This product is recrystallized from methanol (1000 ml) giving the title 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 acetone (100 ml)
  6. temperatureThis material is heated
  7. customgiving a solution
  8. customto 0° C produces a solid which
  9. customis collected
  10. customair dried
  11. dissolutionThis solid is dissolved in ethanol (350 ml)
  12. filtrationfiltered
  13. temperaturecooled
  14. customproducing a gel, which
  15. temperatureThe mixture is cooled to 0° C
  16. customthe product is collected
  17. washwashed with water, and air
  18. customdried
  19. customThis product is recrystallized from methanol (1000 ml)

Sources & evidence

ORD record
ord-86d696f7e588479b9d8821547b9572d0
Source dataset
uspto-grants-1978_11
Patent number
US04126444

Reaction notes

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