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

HRID 540587Notes

Reaction equation

HRID 540587 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+H37Cl 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-5d4080d4e6cb4548b558760a983e9d87
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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