Barbituric Acid → HCID 13372138, compound

HRID 850925Notes

Reaction equation

HRID 850925 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34][NH2:35].N1C(=O)CC(=O)NC1=O>C(Cl)Cl.CO>[C:1]([S:4][CH2:5][CH:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]([NH:9][CH2:10][C:11]([NH:35][CH2:34][CH2:33][N:32]([CH3:36])[CH3:31])=[O:13])=[O:8])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 6211Barbituric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 66053N,N-DimethylethylenediamineHCID 12769072HCID 12769072, compound

Product 1

HCID 13372138HCID 13372138, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A 2.61 g (0.01 mole) sample of (±)-N-[2-(acetylmercaptomethyl)-4-methyl-1-oxopentyl]glycine is slurried in 50 ml of CH2Cl2. Triethylamine (1.08 g, 0.01 mole) is added to give a solution which is cooled to -10° C. and treated with 1.08 g (0.01 mole) of ethyl chloroformate. After 1/2 hour, a solution of N,N-dimethylethylenediamine (0.88 g, 0.01 mole) in 10 ml of CH2Cl2 is added, and stirring from -5° C. to +25° C. continued for 2 hours. The mixture is evaporated and triturated with ethyl acetate. The triethylamine hydrochloride is filtered and the filtrates evaporated to an oil, 3.6 g. A 2.95 g sample of oil is dissolved with 1 equivalent of barbituric acid in methanol, filtered and evaporated to a foam. Addition of acetonitrile gives a white solid which is washed (briefly) with absolute ethanol and then acetonitrile. Recrystallization from 100 ml of acetonitrile gives a white powder, 1.3 g of (±)-N2 -[2-[(acetylthio)methyl]-4-methyl-1-oxopentyl]-N-[2-(dimethylamino)ethyl]glycinamide, barbituric acid (1:1) salt (34%), m.p. 151°-154°, which analyzes correctly for a salt with 1.0 mole of barbituric acid and 0.5 mole of water.

Workup

  1. customto give a solution which
  2. waitcontinued for 2 hours
  3. customThe mixture is evaporated
  4. customtriturated with ethyl acetate
  5. filtrationThe triethylamine hydrochloride is filtered
  6. customthe filtrates evaporated to an oil, 3.6 g
  7. filtrationfiltered
  8. customevaporated to a foam
  9. additionAddition of acetonitrile
  10. customgives a white solid which
  11. washis washed (briefly) with absolute ethanol
  12. customRecrystallization from 100 ml of acetonitrile

Sources & evidence

ORD record
ord-f62e47a8dac84280a14f528ed4484a32
Source dataset
uspto-grants-1983_05
Patent number
US04382081

Reaction notes

Loading…