N-(benzoyloxy)benzamide synthesis

11synthesis methods

Product Name:N-(benzoyloxy)benzamide
CAS Number:959-32-0
Molecular formula:C14H11NO3
Molecular Weight:241.24

582-33-2
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79-37-8
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57479-70-6
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$10.00/1g

959-32-0
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Yield:959-32-0 97%

Reaction Conditions:

with triethylamine in dichloromethane;N,N-dimethyl-formamide;

Steps:

1.a Example 1

(a) Ethyl 3-{(4-chloro-2-methoxybenzoyl)amino}benzoate (4: R_1A=OMe, R₂ and R₄=H, R_3A=Cl, R₅=H and R_A=Et) A suspension of 4-chloro-2-methoxybenzoic acid (10.0 g, 53.6 mmol), oxalyl chloride (8.84 g, 69.7 mmol) and DMF (50 μL) in CH₂Cl₂ (107 mL) was stirred at 25° for 2 h. The resulting clear solution was concentrated under reduced pressure. To the residual, crude acyl chloride in CH₂Cl₂ (107 mL) were added ethyl 3aminobenzoate (8.85 g, 53.6 mmol) and Et₃N (10.8 g, 107 mmol) over 5 min at 25°. The mixture was stirred at 25° for 24 h. The resulting suspension was diluted with EtOAc (350 mL) and the resulting solution was successively washed with aqueous 1 N HCl (2*150 mL), aqueous saturated NaHCO₃ (2*150 mL) and brine (150 mL). The organic layer was dried (MgSO₄), filtered and concentrated under reduced pressure to give the desired benzoylaminobenzoate of formula 4 (17.4 g, 97% yield) as a beige solid: ¹H NMR (DMSO-d₆) δ 810.31 (s, 1H), 8.40 (broad s, 1H), 7.94 (broad d, J=7.9 Hz, 1H), 7.69 (dt, J=7.9, 1.2 Hz, 1H), 7.62 (d, J=8.2 Hz, 1H), 7.49 (t, J=7.9 Hz, 1H), 7.28 (d, J=1.9 Hz, 1H), 7.13 (dd, J=8.2, 1.9 Hz, 1H), 4.33 (q, J=7.0 Hz, 2H), 3.92 (s, 3H), 1.33 (t, J=7.0 Hz, 3H).