Chloromethyl dodecyl ether → Barbituric acid, 1,3-bis((docecyloxy)methyl)-5-ethyl-5-phenyl-

HRID 1413199Notes

Reaction equation

HRID 1413199 reaction equation
[CH3:1][CH2:2][C:3]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10](=[O:11])[N-:9][C:7](=[O:8])[NH:6][C:4]1=[O:5].[Na+].Cl[CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>CN(C)C=O>[CH3:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:21][CH2:20][N:6]1[C:7](=[O:8])[N:9]([CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:10](=[O:11])[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH2:2][CH3:1])[C:4]1=[O:5]

Participants

4

Reactant 2

HCID 12215332Chloromethyl dodecyl etherHCID 12598276Phenobarbital-Natrium

Product 1

HCID 213995Barbituric acid, 1,3-bis((docecyloxy)methyl)-5-ethyl-5-phenyl-Yield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Powdered phenobarbital sodium (25.4 g) was suspended at room temperature in 250 ml of dimethylformamide and 22.1 g of chloromethyldodecanyl ether was added to the suspension. The reaction mixture was stirred overnight and poured into 1 liter of ice-water; the mixture was then stirred for 3 hours and the waxy solid removed by filtration. The wet solid was dissolved in 150 ml of boiling ethanol; to the hot solution 1 g of activated carbon was added and the boiling solution was filtered through a Buchner funnel which contained a compacted layer of finely-divided diatomaceous silica. The filter cake was washed three times with 15 ml of ethanol and the hot solution together with the washings was allowed to cool overnight. The resulting crystals were filtered and recrystallized in the same manner as described for the first crystallization. There was obtained 13 g of N,N'-dilauryloxymethyl phenobarbital (also known as 1,3-dilauryloxymethyl-5-ethyl-5-phenyl barbituric acid), m.p. 48°-50°. When tested as described above the compound exhibited anticonvulsant activity against maximal electroshock, the peak activity occurring at 2 hours and the ED50 being about 50 mg/kg. The LD50 (oral) was determined to be greater than 500 mg/kg.

Workup

  1. stirringthe mixture was then stirred for 3 hours
  2. customthe waxy solid removed by filtration
  3. dissolutionThe wet solid was dissolved in 150 ml of boiling ethanol
  4. additionto the hot solution 1 g of activated carbon was added
  5. filtrationthe boiling solution was filtered through a Buchner funnel which
  6. washThe filter cake was washed three times with 15 ml of ethanol
  7. temperatureto cool overnight
  8. filtrationThe resulting crystals were filtered
  9. customrecrystallized in the same manner
  10. customas described for the first crystallization

Sources & evidence

ORD record
ord-309d67f9447b4a57b54d7514313bcd60
Source dataset
uspto-grants-1981_02
Patent number
US04249005

Reaction notes

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