4-Chlorophenyl Isocyanate → 1-(4-chloro-phenyl)-3-(4-oxo-4H-chromen-6-yl)-urea

HRID 1626166Notes

Reaction equation

HRID 1626166 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[CH:6][C:5]2=[O:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[O:8][CH:7]=[CH:6][C:5]3=[O:12])=[O:22])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 194388266-amino-4H-chromen-4-one

Product 1

HCID 231394541-(4-chloro-phenyl)-3-(4-oxo-4H-chromen-6-yl)-ureaYield 99.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred and heated (80° C.) slurry of 6-aminochromone (3.0 g, 18.6 mmol) in toluene (200 mL) was added 4-chlorophenyl isocyanate (3.2 g, 20.5 mmol) and the mixture was refluxed further for 18 hours. The reaction mixture was cooled and the precipitate was filtered and washed with methanol. The residue was dried in vacuo to afford 1-(4-chloro-phenyl)-3-(4-oxo-4H-chromen-6-yl)-urea (5.8 g, 99%) as a yellow powder. LCMS m/z (%)=315 (M+H35Cl, 100), 317 (M+H37Cl, 32.2) 1H NMR (400 MHz, DMSO-d6) δ: 9.09 (bs, 1H), 8.94 (bs, 1H), 8.29 (d, J=5.99 Hz, 1H), 8.20 (d, J=2.69 Hz, 1H), 7.81 (dd, J=9.0, 2.75 Hz, 1H), 7.62 (d, J=9.07 Hz, 1H), 7.52 (dd, J=6.84, 2.16 Hz, 2H), 7.35 (dd, J=6.85, 2.11 Hz, 2H), 6.33 (d, J=5.98 Hz, 1H).

Workup

  1. temperaturethe mixture was refluxed further for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe precipitate was filtered
  4. washwashed with methanol
  5. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-f3561bc719394c358b8c01a12737fff1
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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