Phenyl isocyanate → N-phenyl-N'-(6-nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxalin-9-yl)urea

HRID 863504Notes

Reaction equation

HRID 863504 reaction equation
[NH2:1][CH:2]1[CH2:20][C:6]2[C:7]3[NH:8][C:9](=[O:19])[C:10](=[O:18])[NH:11][C:12]=3[CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:5]=2[CH2:4][CH2:3]1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>CN(C)C=O>[C:21]1([NH:27][C:28]([NH:1][CH:2]2[CH2:20][C:6]3[C:7]4[NH:8][C:9](=[O:19])[C:10](=[O:18])[NH:11][C:12]=4[CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:5]=3[CH2:4][CH2:3]2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 196962049-Amino-6-nitro-1,4,7,8,9,10-hexahydro-benzo[f]quinoxaline-2,3-dione

Product 1

HCID 19696244N-phenyl-N'-(6-nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxalin-9-yl)urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 15 (0.15 g, 0.5 mmol), phenylisocyanate (0.1 g, 1 mmol) and triethylamine (0.1 g) in 5 mL dimethylformamide were stirred at room temperature for 18 h. The solvent was removed by rotoevaporation and the residue suspended in methanol/dimethylformamide. After heating, the solid was collected by filtration and dried in vacuo. CHN calc'd for C19H17N5O5.0.5H2O.HCON(Me)2 : C, 55.34; H, 5.27: N, 17.60 found-C, 55.38: H, 4.95; N, 17.04. H-NMR (400 MHz, dmso) 1H, s, 12.1; 1H, s, 11.45; 1H, s, 8.4; 1H, s, 7.95; 1H, s, 7.7; 2H, d, 7.4; 2H, t, 7.23; 1H, t, 6.9 1H, d, 6.35; 1H, t, 4.1; +ring protons.

Workup

  1. customThe solvent was removed by rotoevaporation
  2. temperatureAfter heating
  3. filtrationthe solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-46234ec74b73406e8e364aaf0cd3c4c5
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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