4-Chlorophenyl Isocyanate → HCID 67282653, compound

HRID 1616113Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.C(N(CC)CC)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>O1CCOCC1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:4](=[O:6])[C:3]3[C:2](=[CH:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=3)[NH:1][C:31]2=[O:32])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of dimethyl 2-aminoterephthalate (1.50 g, 7.2 mmol) in triethylamine (2.50 mL, 18.0 mmol) and 1,4-dioxane (20 mL) was added 1-chloro-4-isocyanatobenzene (1.4 g, 9.3 mmol). The reaction mixture was heated to 90° C. and stirred overnight. The mixture was then cooled to rt and the solid was filtered, then rinsed with ether (2×) to afford methyl 3-(4-chlorophenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (1.56 g, 66%). LC-MS: (FA) ES+ 331; 1H NMR (300 MHz, DMSO) δ 11.77 (s, 1H), 8.07 (d, J=8.2 Hz, 1H), 7.82 (d, J=1.2 Hz, 1H), 7.74 (dd, J=8.2, 1.4 Hz, 1H), 7.56 (d, J=8.6 Hz, 2H), 7.40 (d, J=8.6 Hz, 2H), 3.92 (s, 3H).

Workup

temperatureThe mixture was then cooled to rt
filtrationthe solid was filtered
washrinsed with ether (2×)

Sources & evidence

ORD record: ord-63a9e40087994d00bb5bd8d22f29d9c1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765773B2

Reaction notes

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