Benzyl chloromethyl ether → 1,3-Bis[(benzyloxy)methyl]-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

HRID 1413201Notes

Reaction equation

HRID 1413201 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([C:6]1([CH2:15][CH:16]=[CH2:17])[C:13](=[O:14])[N-:12][C:10](=[O:11])[NH:9][C:7]1=[O:8])[CH3:5].[Na+].[CH2:19]([O:26][CH2:27]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([O:26][CH2:27][N:9]1[C:7](=[O:8])[C:6]([CH2:15][CH:16]=[CH2:17])([CH:4]([CH2:3][CH2:2][CH3:1])[CH3:5])[C:13](=[O:14])[N:12]([CH2:27][O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]1=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 137983Benzyl chloromethyl etherHCID 14148199309-43-3

Product 1

HCID 2079111,3-Bis[(benzyloxy)methyl]-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium secobarbital (25.5 g.) was dissolved in 250 ml of hot dimethylformamide. The solution was vigorously stirred and allowed to cool to room temperature to provide a fine suspension. To the suspension was added chloromethyl benzyl ether (16.5 g.) over a period of 10 minutes. The reaction mixture was stirred overnight and poured into 500 ml of ice water; the mixture was stirred for 1 hour and was extracted into methylene chloride. The methylene chloride solution was dried and the methylene chloride evaporated under reduced pressure to yield an oil. This crude oil was adsorbed on 60-200 mesh silica gel; elution with a solvent mixture containing 1 part of ethyl acetate and 20 parts of benzene (by volume) provided pure 1,3-dibenzyloxymethyl-5-allyl-5-(2-pentyl) barbituric acid.

Workup

  1. customto provide a fine suspension
  2. stirringThe reaction mixture was stirred overnight
  3. stirringthe mixture was stirred for 1 hour
  4. extractionwas extracted into methylene chloride
  5. dry with materialThe methylene chloride solution was dried
  6. customthe methylene chloride evaporated under reduced pressure
  7. customto yield an oil
  8. washelution with a solvent mixture
  9. additioncontaining 1 part of ethyl acetate and 20 parts of benzene (by volume)

Sources & evidence

ORD record
ord-2815da65f32d4d4194fc7de347bf08b4
Source dataset
uspto-grants-1981_02
Patent number
US04249005

Reaction notes

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