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

HRID 407471Notes

Reaction equation

HRID 407471 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-a8abe4131f6a44c88eb5d71292660c30
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

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