Phenyl isocyanate → 1,2-Dihydro-7-nitro-2-oxo-6-(4-((phenylcarbamoyloxy)methyl)imidazole-1-yl)quinoline-3-carboxylic acid

HRID 412069Notes

Reaction equation

HRID 412069 reaction equation
C([O:3][C:4]1[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([N+:26]([O-:28])=[O:27])=[C:9]([N:19]3[CH:23]=[C:22]([CH2:24][OH:25])[N:21]=[CH:20]3)[CH:10]=2)[N:5]=1)C.[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(OC(C)C)(C)C>ClCCl>[N+:26]([C:8]1[CH:7]=[C:6]2[C:11]([CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:4](=[O:3])[NH:5]2)=[CH:10][C:9]=1[N:19]1[CH:23]=[C:22]([CH2:24][O:25][C:36](=[O:37])[NH:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:21]=[CH:20]1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 7914Diisopropyl EtherHCID 9864967Ethyl 2-ethoxy-6-(4-(hydroxymethyl)imidazole-1-yl)-7-nitroquinoline-3-carboxylate

Product 1

HCID 98683211,2-Dihydro-7-nitro-2-oxo-6-(4-((phenylcarbamoyloxy)methyl)imidazole-1-yl)quinoline-3-carboxylic acidYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 1 (50.0 mg, 129 μmol) in dichloromethane (2 ml) was added phenyl isocyanate (46.2 mg, 388 μmol), and the mixture was stirred overnight at room temperature. Diisopropyl ether was added to the reaction mixture, and the precipitated crystals were collected by filtration and air-dried. These were dissolved into acetic acid (5 ml) and concentrated hydrochloric acid (1 ml) was added, which was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was washed with water and ethyl acetate in sequence and then air-dried, thereby obtaining 41.0 mg of title compound as yellow powder. Yield 71%.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customair-dried
  3. dissolutionThese were dissolved into acetic acid (5 ml) and concentrated hydrochloric acid (1 ml)
  4. additionwas added
  5. stirringwhich was stirred overnight at room temperature
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. washThe residue was washed with water and ethyl acetate in sequence
  8. customair-dried

Sources & evidence

ORD record
ord-43ce8eb9d0da4830b1d2802993a0b36f
Source dataset
uspto-grants-2003_05
Patent number
US06562839B1

Reaction notes

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