ChemicalBook CAS DataBase List 1-(5H-Dibenzo[b,f]azepine-5-yl)ethanone

1-(5H-Dibenzo[b,f]azepine-5-yl)ethanone synthesis

5synthesis methods

Product Name:1-(5H-Dibenzo[b,f]azepine-5-yl)ethanone
CAS Number:19209-60-0
Molecular formula:C16H13NO
Molecular Weight:235.28

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75-36-5 Synthesis

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Yield:19209-60-0 100%

Reaction Conditions:

Stage #1: dibenzoazepinewith sodium hydride in N,N-dimethyl-formamide;mineral oil;Inert atmosphere;
Stage #2: acetyl chloride in N,N-dimethyl-formamide;mineral oil at 23; for 1 h;Inert atmosphere;

Steps:

5-Acetyl-5H-dibenz[b,f]azepine (4); Typical Procedure

To a solution of iminostilbene (2; 965 mg, 5.0 mmol) in DMF (4 mL) at 0 °C under argon were added successively NaH (60% in oil; 240 mg,6.0 mmol) and AcCl (0.47 mL, 6.0 mmol), and the mixture was stirred at 23 °C for 1 h. The reaction was quenched with ice-water and the mixture was extracted with EtOAc. The organic layer was washed with sat. aq NaHCO₃, dried over MgSO₄, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc-hexane, 1:2) to give 4 as a white solid; yield: 1.27 g (quant); mp 106 °C. IR (ATR): 1677 cm^-1. ¹H NMR (600 MHz, CDCl₃): δ = 7.45-7.29 (m, 8 H), 6.96 (d, J = 12 Hz, 1H), 6.90 (d, J = 12 Hz, 1 H), 1.85 (s, 3 H). ¹³C NMR (150 MHz, CDCl₃): δ = 170.8, 140.5, 140.3, 134.7, 133.5, 131.5, 129.3, 129.3, 129.3, 129.2, 129.0, 128.5, 127. 9, 127.9, 127.4, 22.1. HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₆H₁₃NO: 258.0889; found: 258.0886.

References:

Kanase, Yuki;Kuniyoshi, Mai;Tabata, Hidetsugu;Takahashi, Yuka;Kayama, Susumu;Wakamatsu, Shintaro;Oshitari, Tetsuta;Natsugari, Hideaki;Takahashi, Hideyo [Synthesis,2015,vol. 47,# 24,art. no. SS-2015-F0451-OP,p. 3907 - 3913]

256-96-2
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