m-Tolyl isocyanate → HCID 19432592, compound

HRID 1736343Notes

Reaction equation

HRID 1736343 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](=[O:26])[C:21]2[S:25][CH:24]=[CH:23][CH:22]=2)[C:3]1=[O:27].[C:28]1([CH3:37])[CH:33]=[CH:32][CH:31]=[C:30]([N:34]=[C:35]=[O:36])[CH:29]=1>O1CCCC1>[O:27]=[C:3]1[CH:2]([NH:1][C:35]([NH:34][C:30]2[CH:29]=[C:28]([CH3:37])[CH:33]=[CH:32][CH:31]=2)=[O:36])[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](=[O:26])[C:21]1[S:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19432599HCID 19432599, compound

Product 1

HCID 19432592HCID 19432592, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.26 g 3-amino-1,3-dihydro-5-phenyl-1-(2-thenoyl)methyl-2H-1,4-benzodiazepin-2-one, 95 mg 3-tolylisocyanate and 5 ml tetrahydrofuran was stirred at room temperature for two hours. The solvent was distilled off from the reaction mixture under reduced pressure, a 1:1 mixture of toluene and diethyl ether (5 ml) was added to the residue, and the crystals were collected by filtration, thus giving 0.2 g of 1-[2,3-dihydro-2-oxo-5-phenyl-1-(2-thenoyl)methyl-1H-1,4-benzodiazepin-3-yl]-3-(3-tolyl)urea.

Workup

  1. distillationThe solvent was distilled off from the reaction mixture under reduced pressure
  2. additiona 1:1 mixture of toluene and diethyl ether (5 ml)
  3. additionwas added to the residue
  4. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-f501e66b6b6a4a6badf7d2458522e9b3
Source dataset
uspto-grants-1996_07
Patent number
US05541182

Reaction notes

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