F
N. Saraiva Rosa et al.
Paper
Synthesis
13C NMR (125 MHz, DMSO-d6): = 155.6 (CO), 137.9 (CAr), 132.3 (CAr),
127.9 (CAr), 123.3 (CAr), 121.9 (CAr), 112.4 (CAr).
References
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(b) Jagtap, A. D.; Kondekar, N. B.; Sadani, A. A.; Chern, J. W. Curr.
Med. Chem. 2017, 24, 622. (c) Cioffi, C. L.; Dobri, N.; Freeman, E.
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HRMS (ESI-QTOF): m/z [M + Na]+ calcd for C7H8N2OBrNa: 236.9639;
found: 236.9640.
1-(3-Chlorophenyl)urea (9p)
Prepared according to General Procedure A using 3-chlorobenzamide
(77.8 mg, 0.5 mmol). Additional amounts of PIDA (0.5 mmol) and NH3
in MeOH (7 M, 0.60 mL) were added after 4 h and the mixture was left
to stir for an additional 24 h. The mixture was concentrated under re-
duced pressure and the residue was purified by flash chromatography
on silica gel (CH2Cl2/MeOH, 95:5) to afford urea 9p (76.2 mg, 89%) as a
pale brown solid.
Mp 143 °C; Rf = 0.2 (CH2Cl2/MeOH, 95:5).
1H NMR (500 MHz, DMSO-d6): = 8.73 (s, 1 H, NH), 7.69 (t, J = 2.0 Hz,
1 H, CHAr), 7.22 (t, J = 8.2 Hz, 1 H, CHAr), 7.16 (ddd, J = 8.2, 1.9, 1.0 Hz, 1
H, CHAr), 6.92 (ddd, J = 7.8, 2.0, 1.0 Hz, 1 H, CHAr), 5.96 (s, 2 H, NH2).
13C NMR (125 MHz, DMSO-d6): = 155.8 (CO), 142.2 (CAr), 133.1 (CAr),
130.2 (CAr), 120.6 (CAr), 117.0 (CAr), 116.0 (CAr).
HRMS (ESI-QTOF): m/z [M + H]+ calcd for C7H8N2OCl: 171.0325;
found: 171.0325.
2(3H)-Benzoxazolone (9r)
Prepared according to General Procedure A using salicylamide (68.6
mg, 0.5 mmol) and purified by flash chromatography on silica gel
(CH2Cl2/MeOH, 95:5) to afford urea 9r (67 mg, 99%) as a brown solid.
(2) (a) Zakrzewski, J.; Krawczyk, M. Heteroat. Chem. 2006, 17, 393.
(b) Wada, Y.; Kamada, Y.; Hanaki, K. US Patent 5833733, 1998.
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Schönhammer, A.; Hamprecht, G. US Patent 6054410, 2000.
(d) Achgill, R. K.; Call, L. W. US Patent 4987233, 1991. (e) Arnold,
W. R. US Patent 4165229, 1979.
Mp 140 °C; Rf = 0.4 (CH2Cl2/MeOH, 95:5).
IR (ATR): 3201, 1732, 1478, 1253, 937, 686 cm–1
.
1H NMR (500 MHz, DMSO-d6): = 11.6 (s, 1 H, NH), 7.27 (d, J = 8.0 Hz,
1 H, CHAr), 7.12–7.16 (m, 1 H, CHAr), 7.06–7.09 (m, 2 H, CHAr).
13C NMR (125 MHz, DMSO-d6): = 154.4 (CO), 143.3 (CAr), 130.4 (CAr),
123.8 (CAr), 121.8 (CAr), 109.8 (CAr), 109.5 (CAr).
HRMS (ESI-QTOF): m/z [M + H]+ calcd for C7H6NO2: 136.0399; found:
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Funding Information
The authors thank the Centre National de la Recherche Scientifique
(CNRS), Normandie Université (RIN ChemImaging), Labex SynOrg
(Grant No. ANR-11-LABX-0029), the Conseil Régional de Normandie
and the Fonds Européen de Développement Régional (FEDER) for fi-
nancial support.
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(10) Katayama, N.; Fukusumi, S.; Funabashi, Y.; Iwahi, T.; Ono, H.
J. Antibiot. 1993, 46, 606.
Acknowledgment
(11) (a) Lee, S.-H.; Yoshida, K.; Matsushita, H.; Clapham, B.; Koch, G.;
Zimmermann, J.; Janda, K. D. J. Org. Chem. 2004, 69, 8829.
(b) Lee, S.-H.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K.
D. Org. Lett. 2003, 5, 511. (c) Belfrage, A. K.; Gising, J.; Svensson,
F.; Åkerblom, E.; Sköld, C.; Sandström, A. Eur. J. Org. Chem. 2015,
978. (d) Wu, J.; Xie, Y.; Chen, X.; Deng, G.-J. Adv. Synth. Catal.
2016, 358, 3206. (e) Rakesh, K. P.; Ramesha, A. B.; Shantharam,
C. S.; Mantelingu, K.; Mallesha, N. RSC Adv. 2016, 6, 108315.
(f) Rekunge, D. S.; Khatri, C. K.; Chaturbhuj, G. U. Tetrahedron
Lett. 2017, 58, 4304.
We gratefully acknowledged K. Jarsalé for HRMS analyses, and H.
El Slibani and R. Legay for NMR studies carried out at Caen.
Supporting Information
Supporting information for this article is available online at
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(12) Wöhler, F. Ann. Phys. Chem. 1828, 88, 253.
(13) Browne, D. L.; O’Brien, M.; Koos, P.; Cranwell, P. B.; Polyzos, A.;
Ley, S. V. Synlett 2012, 23, 1402.
© 2020. Thieme. All rights reserved. Synthesis 2020, 52, A–G