BENZAMIDE, N-[2-(AMINOCARBONYL)PHENYL]- synthesis
- Product Name:BENZAMIDE, N-[2-(AMINOCARBONYL)PHENYL]-
- CAS Number:18543-22-1
- Molecular formula:C14H12N2O2
- Molecular Weight:240.26
Yield:18543-22-1 99%
Reaction Conditions:
with pyridine in tetrahydrofuran; for 16 h;Inert atmosphere;
Steps:
5 4.2.5 2-Benzamidobenzamide (14a)
Dry pyridine (151 mg, 1.2 mmol) was added to 12 (200 mg, 1.47 mmol) in dry THF (4.0 mL), followed by benzoyl chloride (228 mg, 1.6 mmol) in dry THF (4.0 mL). The mixture was stirred under Ar for 16 h. Evaporation and chromatography (EtOAc/CH2Cl2 2:3) gave 14a (351 mg, 99%) as a white solid: mp 233-235 °C (lit. [61]
mp 234 °C); 1H NMR ((CD3)2SO) δ 7.17-7.19 (1H, m, 5-H), 7.56-7.59 (3 H, m, 4-H + Ar 3,5-H2), 7.63 (1 H, m, Ar 4-H), 7.65 (1 H, br, s, NHH), 7.89 (1 H, dd, J = 8.0, 1.5 Hz, 6-H), 7.94-7.96 (2 H, m, Ar 2,6-H2), 8.43 (1 H, brs, NHH), 8.72 (1 H, dd, J = 8.5, 1.0 Hz, 3-H), 12.96 (1 H, s, NH); 13C ((CD3)2SO) (HSQC/HMBC) δ 119.15 (1-C), 120.00 (3-C), 122.63 (5-C), 126.92 (Ar 2,6-C2), 128.73 (6-C), 128.92 (Ar 3,5-C2), 132.03 (Ar 4-C), 132.58 (4-C), 140.08 (2-C), 134.60 (Ar 1-C), 164.37 (NHCO), 171.15 (CONH2).
References:
Nathubhai, Amit;Haikarainen, Teemu;Hayward, Penelope C.;Mu?oz-Descalzo, Silvia;Thompson, Andrew S.;Lloyd, Matthew D.;Lehti?, Lari;Threadgill, Michael D. [European Journal of Medicinal Chemistry,2016,vol. 118,p. 316 - 327]
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