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Chemical Structure| 32366-02-2 Chemical Structure| 32366-02-2

Structure of 32366-02-2

Chemical Structure| 32366-02-2

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Product Details of [ 32366-02-2 ]

CAS No. :32366-02-2
Formula : C9H10ClNO
M.W : 183.63
SMILES Code : O=C(Cl)N(CC1=CC=CC=C1)C
MDL No. :MFCD18431941

Safety of [ 32366-02-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H335-H314
Precautionary Statements:P260-P264-P270-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 32366-02-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 32366-02-2 ]

[ 32366-02-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 32366-02-2 ]
  • [ 152120-61-1 ]
  • [ 1324007-53-5 ]
YieldReaction ConditionsOperation in experiment
19% To a solution of 29(b)T. Sunazuka, A. Sugawara, K. Iguchi, T. Hirose, K. Nagai, Y. Noguchi, Y. Saito, Y. Yanai, T. Yamamoto, T. Watanabe, K. Shiomi and S. mura, Bioorg. Med. Chem. 17 (2009), pp. 2751-2758. Article | PDF (672 K) | View Record in Scopus | Cited By in Scopus (9)21b (1.10 g, 5.23 mmol) in THF (53 mL) was added 55% NaH, dispersed in paraffin liquid (460 mg, 10.5 mmol) at 0 C. After stirring at 0 C for 10 min, the reaction solution was allowed to warm up to room temperature, and then a solution of N-benzyl-N-methylamidoylchloride (30)32 (2.9 g, 15.8 mmol) in THF (15.8 mL) was introduced to the reaction solution. The resulting mixture was stirred at reflux for 1 h and cooled to room temperature. After the mixture was diluted with EtOAc (110 mL), quenched with satd NH4Cl aq solution (100 mL), and separated, the organic layer was washed with H2O (100 mL×1), dried over Na2SO4, and concentrated to yield the crude product. Flash chromatography (hexane/EtOAc=3/1) afforded 26 (363 mg, 19%) as a colorless oil (Scheme 6). Rf=0.40 (silica gel, hexane/EtOAc=1/2); IR (KBr) nu (cm-1): 2941 (w), 2359 (w), 1761 (s), 1641 (s), 1504 (s), 1242 (s), 1153 (s); 1H NMR (270 MHz, CD3OD) delta (ppm) 8.28 (br d, J=27.4 Hz, 1H), 7.73 (d, J=4.3 Hz, 1H), 7.30 (m, 4H), 6.50 (m, 1H), 4.58 (s, 2H), 2.88 (s, 1.7H, N-CH3, rotamer), 2.84 (s, 1.3H, N-CH3, rotamer), 1.50 (d, J=1.3 Hz, 9H); 13C NMR (67.5 MHz, CD3OD) delta (ppm) 162.6, [151.5, 151.4 -NH-C(O)O-t-Bu, rotamer], 143.9, [142.2, 141.7 -(CH3)N-C(O)-N, rotamer], 138.4, [130.1, 130.0 pyrazole, rotamer], [129.2, 129.1, 128.8, 128.5, 128.0, 127.9 Ph, rotamer], [110.4, 110.3 pyrazole, rotamer], [83.5, 84.4 -OC(CH3)3, rotamer], [54.5, 52.0 Ph-CH2-N(Me)-, rotamer], [35.2, 33.3 -(OC)N-CH3, rotamer], [28.1, 28.0 -OC(CH3)3, rotamer]; HRMS (FAB, NBA matrix) m/z: 358.1876: [(M+H)+, calcd for C18H24O3N5: 358.1879].
  • 2
  • [ 32366-02-2 ]
  • [ 51746-85-1 ]
  • [ 1356960-60-5 ]
YieldReaction ConditionsOperation in experiment
81% With pyridine; at 90℃; for 2h; N-benzyl-N-methvl-4-(pyridin-3-yl)-1 H-imidazole-1 -carboxamide To 3-(IH-imidazol-4-yI)pyridine (0.5 g, 3.44 mmol) and Pyridine (2.5 ml) charge benzyl(methyl)carbamic chloride (0.759 g, 4.13 mmol). The reaction mixture was heated to 90C and stir for lhr. Sample for TLC. Still starting material, more carbamoyl chloride (0.3g, were added. The mixture was stirred for lh and the reaction conversion was checked by TLC (DCM/MeOH, 9:1). No starting material left. The reaction was cooled to room temperature and the pyridine was removed.The mixture was diluted with sat NaHCO3 and DCM. The biphasic mixture was separated. The aqueous layer was washed with DCM.The combined organic layers were washed with sat NaHCO3, dried over Na2SO4, concentrated to dryness. A dark brown solid (1.13g) was obtained.The product was purified by column chromatography on silica gel (eluent: EtOAc thenDCM/MeOH 94:4).A brown solid (0.91g) was obtained in 81% molar yield; purity >95%.13C NMR (150 MHz, CDCI3, 20C) 6: 151.6, 148.5, 146.6, 139.4, 137.5, 135.1, 132.5, 129.2,128.9, 128.3, 127.4, 123.6, 113.9, 54.2, 36.5
 

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