Toluene → N-(8-bromo-5-isoquinolinyl)-N'-(2,4-dichlorobenzyl)urea

HRID 586055Notes

Reaction equation

HRID 586055 reaction equation
[Br:1][C:2]1[C:11]2[CH:10]=[N:9][CH:8]=[CH:7][C:6]=2[C:5]([NH2:12])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH2:28][N:29]=[C:30]=[O:31]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:30]([NH:29][CH2:28][C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[Cl:20])=[O:31])=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 46127082,4-Dichlorobenzyl isocyanateHCID 220326308-Bromoisoquinolin-5-amine

Product 1

HCID 10093879N-(8-bromo-5-isoquinolinyl)-N'-(2,4-dichlorobenzyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8-Bromo-5-isoquinolinamine (120 mg, 0.52 mmol) in THF:toluene (5 mL, 1:4) was treated with 2,4-dichloro-1-(isocyanatomethyl)benzene (108 mg, 0.52 mmol) in THF (0.5 mL). After stirring for 16 hours at room temperature, the mixture was filtered and the filter cake was dried under reduced pressure to provide the title compound. MS (ESI+) m/z 426 (M+H)+; MS (ESI−) m/z 424 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 4.42 (d, 5.8, 2H), 7.22 (t, J 5.8, 1H), 7.65 (m, 1H), 7.91 (d, J 8.5, 1H), 8.02 (d, J 6.1, 1H), 8.22 (d, J 8.5, 1H), 8.69 (d, J 5.8, 1H), 9.01 (s, 1H), 9.44 (s, 1H); Anal. Calcd for C17H12BrCl2N3O.HCl+0.25EtOH: C, 44.41; H, 3.14; N, 8.88. Found: C, 44.80; H, 2.76; N, 8.84.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filter cake was dried under reduced pressure

Sources & evidence

ORD record
ord-8edd87f9011944b9a4ecde119ad70c7a
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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