ChemicalBook CAS DataBase List BENZAMIDE, N-[2-(AMINOCARBONYL)PHENYL]-

BENZAMIDE, N-[2-(AMINOCARBONYL)PHENYL]- synthesis

11synthesis methods

Product Name:BENZAMIDE, N-[2-(AMINOCARBONYL)PHENYL]-
CAS Number:18543-22-1
Molecular formula:C14H12N2O2
Molecular Weight:240.26

98-88-4 Synthesis

98-88-4
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Benzenecarboximidic acid, 2-amino- (9CI)

28144-70-9
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18543-22-1
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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]

55-21-0 Synthesis