Benzenemethanamine, 3-chloro- → N-(3-chlorobenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

HRID 586009Notes

Reaction equation

HRID 586009 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].[N:10]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[C:16]([CH3:23])[N:17]=[CH:18]2)=[C:11]=[O:12]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH:6][C:11]([NH:10][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[C:16]([CH3:23])[N:17]=[CH:18]2)=[O:12]

Participants

4

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-HCID 222283825-Isocyanato-3-methylisoquinoline

Product 1

HCID 22032619N-(3-chlorobenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-chlorobenzylamine (141 mg, 1.0 mmol) in ether (20 mL) was treated with an ethereal solution of 5-isocyanato-3-methylisoquinoline. The precipitate that formed was collected by filtration, washed with diethyl ether, and air-dried to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 9.18 (s, 1H), 8.69 (s, 1H), 8.20 (d, 1H, J=7.8 Hz), 7.75 (s, 1H), 7.70 (d, 1H, J=8.2 Hz), 7.51 (t, 1H, J=7.8 Hz), 7.31-7.43 (m, 4H), 7.10 (m, 1H), 4.38 (d, 2H, J=5.7 Hz), 2.65 (s, 3H); MS (ESI+) m/z 326/328 (M+H, 35Cl/37Cl).

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with diethyl ether
  4. customair-dried

Sources & evidence

ORD record
ord-6f9247bb01e543b381950be0ff49ff2c
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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