ChemicalBook CAS DataBase List 2,4-Diphenylpyrrole

2,4-Diphenylpyrrole synthesis

7synthesis methods

Product Name:2,4-Diphenylpyrrole
CAS Number:3274-56-4
Molecular formula:C16H13N
Molecular Weight:219.28

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Yield:3274-56-4 98%

Reaction Conditions:

with morpholine;sulphur;ammonium acetate in neat (no solvent) at 80; for 0.5 h;Reagent/catalyst;Solvent;Temperature;

Steps:

General Procedure for the Preparation of 2,4-Diarylpyrroles3a-o, Exemplified with 3a

General procedure: A mixture of 4-nitro-1,3-diphenylbutan-1-one (1a, 1 mmol),sulfur (3 mmol), morpholine (3 mmol), and NH4OAc (6 mmol)within a 5 mL round-bottomed flask was magnetically stirred ina silicone oil bath at 80 °C for 30 min. Progress of the reaction was followed by TLC monitoring. Then the reaction mixture wascooled to ambient temperature, H2O (2.5 mL) was added, andthe product was extracted into CH2Cl2 (2 × 2.5 mL). The organiclayer was dried over Na2SO4, filtered, the solvent was removed,and the residue was purified by crystallization from EtOAc. 2,4-Diphenyl-1H-pyrrole (3a) Colorless crystals, mp 176-177 °C, yield 0.214 g, 98%. IR (KBr):3435 (NH), 1598, 1481, 1451, 1411, 1258, 1185, 1157, 1129,1075, 1030, 903, 807, 746, 688 cm-1. 1H NMR (300.1 MHz,DMSO-d6): d = 6.96 (1 H, s, CH), 7.13 (1 H, t, J = 7.5 Hz, CH), 7.18(1 H, t, J = 7.5 Hz, CH), 7.32 (2 H, t, J = 7.5 Hz, 2 × CH), 7.35 (1 H,s, CH), 7.37 (2 H, t, J = 7.6 Hz, 2 × CH), 7.61 (2 H, d, J = 7.5 Hz, 2 ×CH), 7.69 (2 H, d, J = 7.5 Hz, 2 × CH), 11.45 (1 H, br s, NH). 13CNMR (75.5 MHz, DMSO-d6): d = 103.7 (C3H), 117.1 (C5H), 123.9(2 × CH), 124.9 (2 × CH), 125.2 (C4), 125.5 and 126.2 (2 × CH),129.0 (2 × CH), 129.2 (2 × CH), 132.7 and 133.1 (2 × C) 136.2(C2). MS: m/z (%) = 219 (100) [M+], 191 (37), 165 (15), 115 (38),110 (13), 102 (10), 95 (6), 89 (11), 77 (10), 63 (10), 51 (11). HRMS (ES+): m/z calcd for C16H14N [M + H]+: 220.1126; found:220.1124.

References:

Adib, Mehdi;Ayashi, Neda;Heidari, Fatemeh;Mirzaei, Peiman [Synlett,2016,vol. 27,# 11,art. no. ST-2015-D0957-L,p. 1738 - 1742]

201230-82-2 Synthesis