m-Tolyl isocyanate → HCID 10767780, compound

HRID 1736341Notes

Reaction equation

HRID 1736341 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]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[C:3]1=[O:28].[C:29]1([CH3:38])[CH:34]=[CH:33][CH:32]=[C:31]([N:35]=[C:36]=[O:37])[CH:30]=1>O1CCCC1>[O:28]=[C:3]1[CH:2]([NH:1][C:36]([NH:35][C:31]2[CH:30]=[C:29]([CH3:38])[CH:34]=[CH:33][CH:32]=2)=[O:37])[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]1[CH2:19][C:20]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 10785324HCID 10785324, compound

Product 1

HCID 10767780HCID 10767780, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 0.74 g 3-amino-1,3-dihydro-1-phenacyl-5-phenyl-2H-1,4-benzodiazepin-2-one and 5 ml tetrahydrofuran, was added a solution of 0.27 g 3-tolyl isocyanate in 3 ml tetrahydrofuran, and the resulting mixture was stirred at room temperature for four hours. The solvent was distilled off from the reaction mixture, and the residue was recrystallized from a mixture of toluene and n-hexane, thus giving 0.78 g of 1-[2,3-dihydro-2-oxo-1-phenacyl-5-phenyl-1H-1,4-benzodiazepin-3-yl]-3-(3-tolyl)urea.

Workup

  1. distillationThe solvent was distilled off from the reaction mixture
  2. customthe residue was recrystallized from a mixture of toluene and n-hexane

Sources & evidence

ORD record
ord-8943de7be315441ea179383cf19215ce
Source dataset
uspto-grants-1996_07
Patent number
US05541182

Reaction notes

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