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

HRID 2071374Notes

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

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

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

Sources & evidence

ORD record: ord-7c762000f63940eca2bc07af205ffe6b
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04046894

Reaction notes

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