Chlorophenyl isocyanate → 3-(2-Chlorophenylureido)-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one

HRID 482470Notes

Reaction equation

HRID 482470 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH3:17])=[CH:11][C:10]=2[O:18][CH3:19])[C:6]2[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=2[N:4]([CH3:24])[C:3]1=[O:25].[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]=[C:34]=[O:35]>ClCCl>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[O:35])[NH:1][CH:2]1[N:8]=[C:7]([C:9]2[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH3:17])=[CH:11][C:10]=2[O:18][CH3:19])[C:6]2[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=2[N:4]([CH3:24])[C:3]1=[O:25]

Participants

4

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 153796223-Amino-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one

Product 1

HCID 153887333-(2-Chlorophenylureido)-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 56 mg of 3-amino-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one in 10 ml of dichloromethane is added 0.022 ml of 2-chlorophenyl isocyanate and the reaction mixture is then stirred at room temperature overnight. It is concentrated under vacuum and the residue is crystallized from isopropyl ether to give 3-(2-chlorophenylureido)-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one; m.p.=260° C.; Yield=91%.

Workup

  1. concentrationIt is concentrated under vacuum
  2. customthe residue is crystallized from isopropyl ether

Sources & evidence

ORD record
ord-7a74c5af939c4e978aaf9428721f31a2
Source dataset
uspto-grants-1998_08
Patent number
US05798353

Reaction notes

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