Phenyl isocyanate → HCID 18918177, compound

HRID 1290773Notes

Reaction equation

HRID 1290773 reaction equation
Cl.[NH2:2][CH:3]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[C:7]([Cl:20])[CH:6]=[CH:5][C:4]1=2.C(N(CC)CC)C.[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CS(C)=O.CN(C)C=O>[Cl:20][C:7]1[CH:6]=[CH:5][C:4]2[CH:3]([NH:2][C:35]([NH:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:36])[C:15]3[N:14]4[CH:16]=[CH:17][N:18]=[C:13]4[C:12](=[O:19])[NH:11][C:10]=3[C:9]=2[CH:8]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 18918156HCID 18918156, compound

Product 1

HCID 18918177HCID 18918177, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To 0.5 g of 10-amino-7-chloro-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride suspended in 8 ml of dimethyl sulphoxide is added dropwise 0.45 ml of triethylamine, followed by a solution of 0.9 ml of phenyl isocyanate in 2 ml of dimethylformamide. The reaction medium is stirred for 2 hours at a temperature in the region of 20° C. and the precipitate formed is filtered off, washed with water and dried under reduced pressure (1 mmHg; 0.13 kPa) at 50° C. 0.15 g of 7-chloro-10-(3-phenylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is thus obtained, in the form of a white solid the melting point of which is greater than 260° C. (Analysis C20H14ClN5O2 ·0.6 DMF·0.8 H2O % calculated C: 61.31; H: 3.60; Cl: 9.05; N: 17.87; % found C: 61.1; H: 3.5; Cl: 9.4; N: 17.7).

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. washwashed with water
  4. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 50° C

Sources & evidence

ORD record
ord-a250ac629c7f4c4182edae910e35de40
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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