Methane → Imidafenacin

HRID 252623Notes

Reaction equation

HRID 252623 reaction equation
Cl.P(O)(O)(O)=O.[CH3:7][C:8]1[N:9]([CH2:13][CH2:14][C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([NH2:18])=[O:17])[CH:10]=[CH:11][N:12]=1.C>O>[CH3:7][C:8]1[N:9]([CH2:13][CH2:14][C:15]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:16]([NH2:18])=[O:17])[CH:10]=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 66846935HCID 66846935, compound

Product 1

HCID 6433090ImidafenacinYield 76.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a mixture of 32 mL of 1 mol/L hydrochloric acid and 101 mL of purified water, 13.3 g (32.0 mmol) of 4-(2-methyl-1-imidazolyl)-2,2-diphenylbutanamide phosphate obtained in Example 3 were dissolved, and 1.33 g of activated charcoal were added. After stirring for 1 hour, the mixture was filtered through 4 cm-size Kiriyama funnel, in which 2.66 g of cellulose powder was laid and washed with 13 mL of purified water. To the filtrate and washed solutions 130 mL of ethanol were added, and, under stirrings 48 mL of 2 mol/L sodium hydroxide solution were added to neutralize the solution and crystallize out of the solution. After stirring for 1 hour at an inner temperature of below 15° C. under cooling with ice water, the crystals were collected by filtration and washed with 50 mL of 40% ethanol, then with each 200 mL of purified water five times (fifth washed solution: pH 8.80). Into 53 mL of ethanol, 10.6 g of wet crystals were dissolved completely by heating, and the solution was stirred for 1 hour at room temperature to crystallize out of the solution, followed by cooling with ice water. After stirring for 1 hour at an inner temperature of below 15° C., the crystals were collected by filtration and washed with 5 mL of ethanol. The crystals were dried for 3 hours at 60° C. under reduced pressure (vacuum pump) to obtain 7.80 g (yield: 76.3%) of 4-(2-methyl-1-imidazolyl)-2,2-diphenylbutanamide as white crystalline powder.

Workup

  1. dissolutionwere dissolved
  2. filtrationthe mixture was filtered through 4 cm-size Kiriyama funnel, in which 2.66 g of cellulose powder
  3. washwashed with 13 mL of purified water
  4. washTo the filtrate and washed solutions 130 mL of ethanol
  5. additionwere added
  6. additionunder stirrings 48 mL of 2 mol/L sodium hydroxide solution were added
  7. customcrystallize out of the solution
  8. stirringAfter stirring for 1 hour at an inner temperature of below 15° C.
  9. temperatureunder cooling with ice water
  10. filtrationthe crystals were collected by filtration
  11. washwashed with 50 mL of 40% ethanol
  12. dissolutionInto 53 mL of ethanol, 10.6 g of wet crystals were dissolved completely
  13. temperatureby heating
  14. stirringthe solution was stirred for 1 hour at room temperature
  15. customto crystallize out of the solution
  16. temperatureby cooling with ice water
  17. stirringAfter stirring for 1 hour at an inner temperature of below 15° C.
  18. filtrationthe crystals were collected by filtration
  19. washwashed with 5 mL of ethanol
  20. customThe crystals were dried for 3 hours at 60° C. under reduced pressure (vacuum pump)

Sources & evidence

ORD record
ord-400ce2786ffd4c7ea2623648ef799eec
Source dataset
uspto-grants-2011_01
Patent number
US07868183B2

Reaction notes

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