Phthalic Anhydride → 1-Cyclohexyl-5-ethyl-5-phthalimidobarbituric acid

HRID 1020153Notes

Reaction equation

HRID 1020153 reaction equation
[NH2:1][C:2]1([CH2:17][CH3:18])[C:7](=[O:8])[N:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5](=[O:15])[NH:4][C:3]1=[O:16].N(C1(CC)C(=O)N(C2CCCCC2)C(=O)NC1=O)=[N+]=[N-].[C:39]1(=O)[O:44][C:42](=[O:43])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12>C(O)(=O)C>[CH:9]1([N:6]2[C:7](=[O:8])[C:2]([CH2:17][CH3:18])([N:1]3[C:42](=[O:43])[C:41]4=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]4[C:39]3=[O:44])[C:3](=[O:16])[NH:4][C:5]2=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 154249335-Azido-1-cyclohexyl-5-ethylbarbituric acidHCID 154249365-Amino-1-cyclohexyl-5-ethylbarbituric acid

Product 1

HCID 101345581-Cyclohexyl-5-ethyl-5-phthalimidobarbituric acidYield 61.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of about 500 mg (about 2 mmol) of 5-amino-1-cyclohexyl-5-ethylbarbituric acid available from 5-azido-1-cyclohexyl-5-ethylbarbituric acid as described in Guetschow, M. et al., Synthesis, 1999, 410-414 (incorporated herein by reference) and about 300 mg (about 2 mmol) of phthalic anhydride and about 20 mL of glacial acetic acid was refluxed for about 5 hours. The mixture was cooled to room temperature and the precipitate was filtered off. The precipitate was next washed with H2O and dried to give about 470 mg of 1-cyclohexyl-5-ethyl-5-phthalimidobarbituric acid (a yield of about 61%). The 1-cyclohexyl-5-ethyl-5-phthalimidobarbituric acid had a melting point of about 248 to about 253° C.

Workup

  1. customet al., Synthesis, 1999, 410-414 (
  2. temperaturewas refluxed for about 5 hours
  3. filtrationthe precipitate was filtered off
  4. washThe precipitate was next washed with H2O
  5. customdried

Sources & evidence

ORD record
ord-bdccf1e377dd46f8b5e517fe86bb3744
Source dataset
uspto-grants-2014_05
Patent number
US08716315B2

Reaction notes

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