Phenyl isocyanate → HCID 57075789, compound

HRID 581703Notes

Reaction equation

HRID 581703 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:11][C:12]1[CH:13]=[C:14]2[C:24]([CH2:25][CH:26]=1)=[C:17]1[NH:18][C:19](=[O:23])[C:20](=[O:22])[NH:21][C:16]1=[CH:15]2.C(N(CC)CC)C>CN(C)C=O>[C:1]1([NH:7][C:8](=[O:9])[NH:11][C:12]2[CH:13]=[C:14]3[C:24]([CH2:25][CH:26]=2)=[C:17]2[NH:18][C:19](=[O:23])[C:20](=[O:22])[NH:21][C:16]2=[CH:15]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 86754195HCID 86754195, compound

Product 1

HCID 57075789HCID 57075789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.92 ml of phenyl isocyanate are added at a temperature in the region of 20° C. to a solution of 1.5 g of 7-amino-1,4-dihydro-5H-indeno [1,2-b]pyrazine-2,3-dione hydrochloride and 2.48 ml of triethylamine in 20 ml of dimethylformamide. After overnight stirring at the same temperature, the precipitate formed is filtered off, washed with water and dried under a partial vacuum (1 mm Hg; 0.13 kPa) at 40° C. to yield 1.4 g of 7-(3-phenylureido)-1,4-dihydro-5H-indeno[1,2-b]pyrazine-2,3-dione in the form of a greenish solid, the melting point of which is above 260° C. (Analysis C18H14N4O3 ; 4.0 H2O; % calculated C: 64.66; H: 4.22; N: 16.76; % found C: 64.4; H: 4.5; N: 16.8; 1H NMR spectrum [250 MHz, (CD3)2SO-d6, δ in ppm]: 3.58 (s, 2H CH2 9); 7.00 (t, J=7.5 Hz, 1H: aromatic H of the phenyl at para with respect to the ureido); 7.30 (t, J=7.5 Hz, 2H: aromatic H of the phenyl at meta with respect to the ureido); 7.50 (d, J=7.5 Hz, 2H: aromatic H of the phenyl at ortho with respect to the ureido); from 7.20 to 7.60 (mt, 2H: H 5 and H 6); 7.72 (s broad, 1H: H 8); 8.80 (s broad, 2H: ArNHCONH); 12.00 and 12.28 (2 unres. comp. 1H each: NHCOCONH).

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. washwashed with water
  4. customdried under a partial vacuum (1 mm Hg; 0.13 kPa) at 40° C.

Sources & evidence

ORD record
ord-da03189a6ede48a4b4780a09b702512b
Source dataset
uspto-grants-1999_07
Patent number
US05922716

Reaction notes

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