ChemicalBook CAS DataBase List 1-TRITYLIMIDAZOLE-2-CARBOXALDEHYDE

1-TRITYLIMIDAZOLE-2-CARBOXALDEHYDE synthesis

7synthesis methods

Product Name:1-TRITYLIMIDAZOLE-2-CARBOXALDEHYDE
CAS Number:67478-50-6
Molecular formula:C23H18N2O
Molecular Weight:338.4

76-83-5 Synthesis

76-83-5
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$6.00/25g

10111-08-7 Synthesis

10111-08-7
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$6.00/1g

67478-50-6
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$56.00/250mg

Yield:67478-50-6 81%

Reaction Conditions:

Stage #1: 2-imidazolecarbaldehydewith triethylamine in N,N-dimethyl-formamide at 20; for 0.25 h;
Stage #2: trityl chloride in N,N-dimethyl-formamide; for 48 h;

Steps:

5.1.22. 1-Triphenylmethyl-1H-imidazol-2-carbaldehyde (38)

1H-Imidazol-2-carbaldehyde (36) (1.98 g, 20.0 mmol) in DMF (20 mL) was treated with NEt₃ (4.10 g, 40.0 mmol, 5.62 mL). The mixture was stirred for 15 min at rt before triphenylmethyl chloride (37) (6.26 g, 22.0 mmol), suspended in DMF (10 mL), was added. After stirring for 48 h the solution was diluted with EtOAc (20 mL/mmol) and washed with brine, sat. Na₂CO₃-solution and H₂O. The organic layers were dried over MgSO₄, filtered and concentrated. The crude product was purified by CC (n-Pentane/EtOAc = 6/4).Colourless crystals; Yield: 5.59 g (81%); mp 190 °C. IR (KBr) ν cm^-1: 3397, 3065, 2845, 1708, 1491, 1442, 1396, 1356, 1242, 1169; 500 MHz ¹H NMR (CD₃OD): δ = 7.01 (s, 1H, CH[_5H-Imid.]), 7.09-7.11 (m, 6H, CH_ar), 7.24-7.36 (m, 10H, CH_ar, CH[_4H-Imid.]), 9.21 (s, 1H, CHO); 126 MHz ¹³C NMR (CDCl₃): δ = 76.9 (C(C₆H₅)₃), 126.9 (CH_ar), 128.1 (CH_ar), 129.6 (CH[_4C-Imid.], CH[_5C-Imid.]), 142.1 (C[_2C-Imid.]), 145.6 (C_q), 178.6 (CHO); MS (CI, CH₅⁺): m/z (%) = 338 (1) [M⁺+1], 243 (100), 167 (109); MS (FAB, NBA): m/z (%) = 339.2 (5) [M⁺+1], 243.2 (100), 165.1 (11); HMRS (ESI) calcd. for C₂₃H₁₈N₂ONa₁: 361.1317; found 361.1313.

References:

Hack, Silke;W?rlein, Babette;H?fner, Georg;Pabel, J?rg;Wanner, Klaus T. [European Journal of Medicinal Chemistry,2011,vol. 46,# 5,p. 1483 - 1498] Location in patent:experimental part