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

HRID 919502Notes

Reaction equation

HRID 919502 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 the slurry of 6-aminochromone (3.0 g, 18.6 mmol) stirred and heated to 80° C. in toluene (200 mL) was added 4-chlorophenyl isocyanate (3.2 g, 20.5 mmol) and the mixture was refluxed for 18 hrs. The reaction mixture was cooled and the precipitate was filtered and washed with methanol. The residue was dried in vacuo to afford a yellow powder (5.8 g, 99%) of 1-(4-chloro-phenyl)-3-(4-oxo-4H-chromen-6-yl)-urea. LCMS m/z (%)=315 (M+H, 35Cl 100), 317 (M+H, 37Cl 32.2) 1H NMR (400 MHz, DMSO-d6) δ: 9.098 (bs, 1H), 8.94 (bs, 1H), 8.28-8.30 (d, J=5.99 Hz, 1H), 8.20-8.21 (d, J=2.69 Hz, 1H), 7.81-7.84 (dd, J=9.0, 2.75 Hz, 1H), 7.62-7.64 (d, J=9.07 Hz, 1H), 7.52-7.55 (dd, J=6.84, 2.16 Hz, 2H), 7.35-7.37 (dd, J=6.85, 2.11 Hz, 2H), 6.33-6.34 (d, J=5.98 Hz, 1H).

Workup

  1. temperaturethe mixture was refluxed for 18 hrs
  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-b7db20601e034ed6a1ba94d3044c7637
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

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