Water → 5-Butyl barbituric acid

HRID 373534Notes

Reaction equation

HRID 373534 reaction equation
[CH2:1]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7])CCC.C(Cl)(=O)CC(Cl)=[O:18].C(N(CC)CC)C.[OH2:29]>C(OCC)C>[CH2:13]([CH:14]1[C:1](=[O:29])[NH:5][C:6](=[O:7])[NH:8][C:9]1=[O:18])[CH2:12][CH2:11][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 74269Propanedioyl dichlorideHCID 96940N'-Butyl-N-phenylcarbamimidic acid

Product 1

HCID 747715-Butyl barbituric acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

A quantity of 3.85 g of 1-t.butyl-3-phenylurea is stirred at 0° C. in 50 ml of dry diethyl ether. 1.95 ml of malonylchloride are slowly added dropwise to this solution. After the addition of a little triethylamine the reaction mixture is slowly heated to approximately 30° C. After 2 hours 50 ml of water are added. The ether layer is separated, washed with water, dried and evaporated. After recrystallisation from ethanol, 1-phenyl-3-t.butyl-barbituric acid is obtained in a yield of 0.6 g; melting-point 118°-125° C. The resulting product is acetylated as described in Example III, the title compound (28) being obtained; melting-point 145°-148° C.

Workup

  1. customThe ether layer is separated
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customAfter recrystallisation from ethanol, 1-phenyl-3-t

Sources & evidence

ORD record
ord-53e4070c15a24777ab2ebffe8e32e760
Source dataset
uspto-grants-1992_11
Patent number
US05164396

Reaction notes

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