4-Methoxy-2-methylphenyl isocyanate → N-(7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methoxy-2-methylphenyl)-urea

HRID 2223064Notes

Reaction equation

HRID 2223064 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:5]=2[N:4]([CH3:20])[C:3]1=[O:21].[N:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[CH3:33])=[C:23]=[O:24]>ClCCl>[Cl:19][C:16]1[CH:17]=[CH:18][C:5]2[N:4]([CH3:20])[C:3](=[O:21])[CH:2]([NH:1][C:23]([NH:22][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[CH3:33])=[O:24])[N:8]=[C:7]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 27349054-Methoxy-2-methylphenyl isocyanateHCID 221352663-amino-7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one2×

Product 1

HCID 10151750N-(7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methoxy-2-methylphenyl)-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-7-chloro-5-phenyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (INTERMEDIATE 1) (0.299 g, 1 mmol) in dichloromethane (15 ml) was added 1-isocyanato-4-methoxy-2-methyl-benzene (0.163 g, 1 mmol). The reaction mixture was stirred at room temperature for 17 hours. The solvent was evaporated in vacuo, the residue was triturated with ether and the title compound was obtained as a colorless solid (0.197 g, 42%). 1H-NMR (CDCl3): δ 7.57-7.48 (m, 3H), 7.47-7.44 (m, 1H), 7.39-7.38 (m, 3H), 7.36-7.29 (m, 2H), 6.77-6.73 (m, 2H), 6.71 (d, J=2.8 Hz, 1H), 6.61 (s, 1H), 5.51 (d, J=8.4 Hz, 1H), 3.78 (s, 3H), 3.39 (s, 3H) and 2.29 (s, 3H). MS (ESI) (M+H)+=463.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-2cd7c575798e464190ab7f0e56a06a86
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

Loading…