2,4-Difluorophenyl isocyanate → HCID 9978893, compound

HRID 1656421Notes

Reaction equation

HRID 1656421 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[NH2:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:20][C:19]([Cl:29])=[CH:18][CH:17]=2>O1CCCC1>[Cl:29][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH:12][C:10]([NH:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])=[O:11])=[C:22]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 9992508HCID 9992508, compound

Product 1

HCID 9978893HCID 9978893, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Difluorophenyl isocyanate (0.24 ml) was added to a solution of 3-amino-6-chloro-4-phenylquinoline (509 mg) in anhydrous tetrahydrofuran (8 ml), and the mixture was allowed to stand at room temperature for 20 hrs. The precipitated crystals were collected by filtration. The filtrate was concentrated and the precipitated crystals were collected by filtration. Thus obtained crystals were combined and recrystallized from ethanol to give 6-chloro-3-[3-(2,4-difluorophenyl)ureido]-4-phenylquinoline as colorless crystals (638 mg, 77.8 %). m.p. 206°14 207° C.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. concentrationThe filtrate was concentrated
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-75cd408b28674752a9536f48d0f28e29
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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