Barbituric Acid → HCID 136122890, compound

HRID 2188780Notes

Reaction equation

HRID 2188780 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C(N(CC)C(C)C)(C)C.[N:19]([CH2:22][C:23]([O:25]CC)=[O:24])=[C:20]=[O:21]>ClCCl.CN(C=O)C>[OH:6][C:5]1[NH:4][C:2](=[O:3])[NH:1][C:8](=[O:9])[C:7]=1[C:20]([NH:19][CH2:22][C:23]([OH:25])=[O:24])=[O:21]

Participants

6

Reactant 3

HCID 6211Barbituric AcidHCID 76283Ethyl isocyanatoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 136122890HCID 136122890, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Barbituric acid (512 mg, 4 mmol) was dissolved in a mixture of dichloromethane (3 mL) and DMF (5 mL). N,N-Diisopropylethylamine (2 mL) was added followed by ethyl isocyanatoacetate (645 mg, 5 mmol) and the solution was stirred overnight. After evaporation of all volatiles, the residue was re-dissolved in a mixture of ethanol (5 mL) and 1M aqueous NaOH (5 mL). After stirring at room temperature for one hour, this solution was neutralized by addition of 1M aqueous HCl. The resulting solid was collected, washed with water, and dried under vacuum overnight to give the title compound (202 mg, 22%). LC/MS m/z 230 (M+H+).

Workup

  1. customAfter evaporation of all volatiles
  2. dissolutionthe residue was re-dissolved in a mixture of ethanol (5 mL) and 1M aqueous NaOH (5 mL)
  3. stirringAfter stirring at room temperature for one hour
  4. additionthis solution was neutralized by addition of 1M aqueous HCl
  5. customThe resulting solid was collected
  6. washwashed with water
  7. customdried under vacuum overnight

Sources & evidence

ORD record
ord-8b2d8540f0824a4aa20797ac030505ea
Source dataset
uspto-grants-2012_12
Patent number
US08324208B2

Reaction notes

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