2H-Naphth[2,3-d]imidazol-2-one,1,3-dihydro-(8CI,9CI) synthesis

5synthesis methods

Product Name:2H-Naphth[2,3-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)
CAS Number:5649-76-3
Molecular formula:C11H8N2O
Molecular Weight:184.19

771-97-1 Synthesis

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57-13-6 Synthesis

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2H-Naphth[2,3-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)

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Yield: 84%

Reaction Conditions:

for 0.25 h;Microwave irradiation;

Steps:

lH-naphtho[2,3-d] imidazol-2(3H)-one (7).
lH-naphtho[2,3-d] imidazol-2(3H)-one (7). According to a previously described method, (Kidwai et al., 2005) 2,3-diaminonapthalene (430 mg, 2.77 mmol) and urea (218 mg, 3.63 mmol) were added to a 100 mL Erlenmeyer flask. The flask was heated for 15 min in a 700W kitchen microwave, with stopping every 5 minutes to break up and stir the chunky bronze-colored reaction mixture. The product was suspended in 5% aqueous HCl, and the precipitate was filtered off and washed twice more with 5% HCl and twice with water. The gold-colored solid was then dried under vacuum to yield product (84% yield). NMR (DMSO-de): 10.797 (s, 1.9 H), 7.80 (m, 2H), 7.28 (m, 4H). ¹³C NMR (DMSO-de): 156.14, 131.00, 129.16, 123.22, 103.55. ESI-MS: M+H⁺ calc'd 185.0709, found 185.0711.

References:

ETH ZURICH;STURLA, Shana;TRANTAKIS, Ioannis;DAHLMANN, Heidi WO2015/162130, 2015, A1 Location in patent:Page/Page column 29-30

201230-82-2 Synthesis