Methane → Prinomide Tromethamine

HRID 1110850Notes

Reaction equation

HRID 1110850 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:20])[CH:8]([C:11](=[O:19])[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]#[N:10].[NH2:21][C:22]([CH2:27][OH:28])([CH2:25][OH:26])[CH2:23][OH:24].C>C(O)C>[NH2:21][C:22]([CH2:27][OH:28])([CH2:25][OH:26])[CH2:23][OH:24].[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:20])[CH:8]([C:11](=[O:19])[NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:9]#[N:10]

Participants

5

Reactant 3

HCID 297MethaneHCID 6503Tris(hydroxymethyl)aminomethaneHCID 60352Prinomide

Product 1

HCID 3033812Prinomide Tromethamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 13.36 g of 1-methyl-beta-oxo-alpha-(phenylcarbamoyl)-2-pyrrolepropionitrile and 6.06 g of tromethamine in 100 ml of ethanol is heated to reflux for about one half hour, the solution is allowed to cool to about room temperature, treated with activated charcoal, filtered and reduced to a volume of about 45 ml at a temperature below 60°. The solution is heated to about 50°-55°, 100 ml of toluene is slowly added over a period of about one half hour with stirring and the resulting mixture is slowly cooled to about 15° over a period of one hour and stirred at 15° about 1 hour. The resulting crystalline product is collected by filtration, washed with toluene and dried at 70°-80° under low vacuum for 24 hours to yield 1-methyl-beta-oxo-alpha-(phenylcarbamoyl)-2-pyrrolepropionitrile tromethamine salt of Example 1. Second crop can be obtained by evaporating mother liquor to dryness and crystallizing more product from ethanol: toluene (1:2) as described above.

Workup

  1. temperatureis heated
  2. temperatureto reflux for about one half hour
  3. temperatureto cool to about room temperature
  4. filtrationfiltered
  5. customreduced to a volume of about 45 ml at a temperature below 60°
  6. temperatureThe solution is heated to about 50°-55°
  7. addition100 ml of toluene is slowly added over a period of about one half hour
  8. temperaturethe resulting mixture is slowly cooled to about 15° over a period of one hour
  9. stirringstirred at 15° about 1 hour
  10. filtrationThe resulting crystalline product is collected by filtration
  11. washwashed with toluene
  12. customdried at 70°-80° under low vacuum for 24 hours

Sources & evidence

ORD record
ord-c01cb54ecc8b40ecade434d004ef137b
Source dataset
uspto-grants-1990_12
Patent number
US04977181

Reaction notes

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