Chloromethyl dodecyl ether → Barbituric acid, 1,3-bis((dodecyloxy)methyl)-5,5-diethyl-

HRID 1413200Notes

Reaction equation

HRID 1413200 reaction equation
[CH3:1][CH2:2][C:3]1([CH2:12][CH3:13])[C:9](=[O:10])[N:8]=[C:7]([O-:11])[NH:6][C:4]1=[O:5].[Na+].[CH2:15]([O:27][CH2:28]Cl)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CN(C)C=O>[CH2:15]([O:27][CH2:28][N:8]1[C:9](=[O:10])[C:3]([CH2:12][CH3:13])([CH2:2][CH3:1])[C:4](=[O:5])[N:6]([CH2:28][O:27][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:7]1=[O:11])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 12215332Chloromethyl dodecyl etherHCID 23681217Barbital Sodium

Product 1

HCID 207910Barbituric acid, 1,3-bis((dodecyloxy)methyl)-5,5-diethyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Sodium barbital (4.0 g.) was suspended in 50 ml of dimethylformamide. To the suspension was added, over a period of 5 minutes, chloromethyl n-dodecyl ether (10 g.). The suspension was heated at 110° C. for a period of 1 hour and then allowed to stand overnight without heating. The suspension was poured into 500 ml of ice water and the resulting aqueous emulsion was extracted with ethyl acetate. The ethyl acetate solution was dried and the ethyl acetate was evaporated under reduced pressure to yield an oil, which was purified by column chromatography using silica gel (70-325 mesh). Elution with benzene provided 1,3-di-n-dodecyloxymethyl-5,5-diethyl barbituric acid.

Workup

  1. additionTo the suspension was added, over a period of 5 minutes
  2. temperaturewithout heating
  3. extractionthe resulting aqueous emulsion was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried
  5. customthe ethyl acetate was evaporated under reduced pressure
  6. customto yield an oil, which
  7. customwas purified by column chromatography
  8. washElution with benzene

Sources & evidence

ORD record
ord-0ec5aa6d48e74638989bc88a2e5a5ac5
Source dataset
uspto-grants-1981_02
Patent number
US04249005

Reaction notes

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