Dimethoxymethane → T-2000

HRID 1071465Notes

Reaction equation

HRID 1071465 reaction equation
CO[CH2:3][O:4][CH3:5].[C:6](CS([O-])(=O)=O)(=[O:8])C.[C:14]1([C:20]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:25](=[O:26])[NH:24][C:23](=[O:27])[NH:22][C:21]2=[O:28])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:35](N(CC)C(C)C)(C)C>CN(C)C=O.Cl.C(OCC)(=O)C>[CH3:35][O:8][CH2:6][N:22]1[C:21](=[O:28])[C:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:25](=[O:26])[N:24]([CH2:3][O:4][CH3:5])[C:23]1=[O:27]

Participants

8

Reactant 4

HCID 8020DimethoxymethaneHCID 464845,5-Diphenylbarbituric acidHCID 81531DiisopropylethylamineHCID 161641Dihydroxyacetone sulfate

Product 1

HCID 9907289T-2000

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Dimethoxymethane (10.85 g) was added at 0° C. to 19.7 g of acetylmethanesulfonate. The reaction was stirred at 25° C. for 2 hours. The resultant solution was then added gradually over 45 minutes to a mixture of 10 g of 5,5-diphenylbarbituric acid and 13.85 g of N,N-diisopropyl ethyl amine in 60 ml of dry dimethylformamide. The resultant reaction mixture was stirred for about 15 minutes and then diluted with 180 ml of 2 N HCl, followed by 300 ml of ethyl acetate. The phases were separated and the ethyl acetate phase was washed first with 150 ml of saturated aqueous sodium chloride and then with 150 ml of 2N aqueous NaOH. The organic (ethyl acetate) phase was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give 12.2 g of N,N′-bismethoxymethyl-5,5-diphenylbarbituric acid. Crystallization from 48 ml of toluene afforded 10.5 g of pure product (79.6% yield).

Workup

  1. customThe resultant reaction mixture
  2. stirringwas stirred for about 15 minutes
  3. customThe phases were separated
  4. washthe ethyl acetate phase was washed first with 150 ml of saturated aqueous sodium chloride
  5. dry with materialThe organic (ethyl acetate) phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-08efc46fbe5446ada323ddb2a1f33f60
Source dataset
uspto-grants-2005_06
Patent number
US06906079B2

Reaction notes

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