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Chemical Structure| 897771-13-0 Chemical Structure| 897771-13-0

Structure of 897771-13-0

Chemical Structure| 897771-13-0

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Product Details of [ 897771-13-0 ]

CAS No. :897771-13-0
Formula : C15H11NO3S
M.W : 285.32
SMILES Code : O=C(C1=CC=C(C(N2)=C1)SC3=CC=CC=C3C2=O)OC
MDL No. :MFCD03830198

Safety of [ 897771-13-0 ]

Application In Synthesis of [ 897771-13-0 ]

* 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 [ 897771-13-0 ]

[ 897771-13-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 440627-14-5 ]
  • [ 74-88-4 ]
  • [ 897771-13-0 ]
YieldReaction ConditionsOperation in experiment
86% A solution of ll-Oxo-10,ll-dihydro-dibenzo [b,fj[l,4] thiazepine-8- carboxylic acid (715 mg, 2.61 mmol) and Na2CO3 (1.39 g, 13.05 mmol) in DMF (20 mL) was stirred at room temperature for 0.5 hour. Then CH3I (0.81 mL, 13.05 mmol) was added and the two phase mixture was stirred for another 0.5 hour at room temperature. DMF was then removed at reduce pressure using oil pump and the resulting residue was dissolved in EtOAc. The organic phase was washed with NaHCO3 (aq. sat.), brine, dried (Na2SO3), EPO <DP n="74"/>filtered and evaporated to give crude product. Purification by recrystallization from Toluene afforded 640 mg (86%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): delta 9.23 (IH, bs), 7.88-7.86 (2H, m), 7.79-7.77 (IH, m), 7.64 (IH, J = 8.0Hz), 7.52-7.50 (IH, m), 7.45-7.38 (2H, m), 3.91 (3H, s). 13C NMR (100 MHz, CDCl3): delta 169.4, 165.9, 139.6, 136.8, 136.4, 135.8, 133.3, 132.7, 132.3, 132.2, 131.8, 129.3, 127.0, 123.7, 52.7.
  • 2
  • [ 440627-14-5 ]
  • [ 18107-18-1 ]
  • [ 897771-13-0 ]
YieldReaction ConditionsOperation in experiment
1.23 g In tetrahydrofuran; at 20℃; for 1h; Amine 47 (19.12 g, 0.0602 mol) was dissolved in THF (425 mL) containing H2O (75 mL). The mixture was cooled to 0 C and LiOH·H2O (7.58 g, 0.181 mol) was added in one portion. After 1 h, the reaction was warmed to rt. HPLC or TLC monitoring indicated that hydrolysis was complete after 36 h at rt. The pH was adjusted to 4.0 by the addition of 2 M HCl. The remaining mixture was dried to an off white powder by rotary evaporation followed by lyophilization with MeOH (6 × 300 mL). The resulting powder was further dried by rotary evaporation with toluene (3 × 300 mL) and suspended in DMF (400 mL). After cooling to -20 C, 1,1'-carbonyl-diimidazole (48.84 g, 0.301 mol) was added in portions over 3 h. The flask was equipped with a drying tube filled Drierite. The reaction was warmed to rt over 2 h. After 24 h of vigorous stirring at rt, reaction was cooled to 0 C and methanol (200 mL) was added. The reaction was warmed over 1 h to rt and stirred for an addition 12 h. The contents of the flask were then diluted in EtOAc (200 mL) and filtered with 1:10 MeOH/EtOAc (2 L) through a DCVC column charged with 250 g of Celite (packed at top of column) and 500 g of silica gel (packed at bottom of column). The elutant was concentrated on a rotary evaporator. Recrystallization from a minimal amount hot toluene followed by slow cooling to rt and storage at 4 C for 24 h provided 14.21 g (83%) of methyl ester 50 as a white powder. The remaining mother liquor contained a mixture of 50 and its corresponding acid 49 that could be converted to 50 (1.23 g, 6% yield) by treatment with 0.5 M TMSCH2N2 in THF. This recycled material was not tabulated in the yield. Mp 179-181 C, 1H NMR (500 MHz, CDCl3) delta 8.48 (s, 1H, NH), 7.85 (dd, J = 1.9, 7.4 Hz, 1H); 7.79 (d, J = 1.7 Hz, 1H); 7.77 (dd, J = 1.7, 8.0 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.49 (dd, J = 1.5, 7.5 Hz, 1H), 7.40 (ddd, J = 1.6, 8.3, 11.4 Hz, 1H), 7.39 (ddd, J = 1.6, 8.4, 8.7 Hz, 1H), 3.89 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 170.2. 166.3, 140.1, 137.2, 136.8, 136.0, 133.5, 133.0, 132.5, 132.5, 132.0, 129.6, 127.3, 124.2, 53.1; HREIMS [M+Na]+ m/z: 308.0489 (calcd for C15H11NNaO3S, 308.0357).
  • 3
  • [ 67-56-1 ]
  • C17H11N3O2S [ No CAS ]
  • [ 897771-13-0 ]
  • [ 440627-14-5 ]
YieldReaction ConditionsOperation in experiment
14.21 g With dmap; In N,N-dimethyl-formamide; at 0 - 20℃; for 13h; Amine 47 (19.12 g, 0.0602 mol) was dissolved in THF (425 mL) containing H2O (75 mL). The mixture was cooled to 0 C and LiOH·H2O (7.58 g, 0.181 mol) was added in one portion. After 1 h, the reaction was warmed to rt. HPLC or TLC monitoring indicated that hydrolysis was complete after 36 h at rt. The pH was adjusted to 4.0 by the addition of 2 M HCl. The remaining mixture was dried to an off white powder by rotary evaporation followed by lyophilization with MeOH (6 × 300 mL). The resulting powder was further dried by rotary evaporation with toluene (3 × 300 mL) and suspended in DMF (400 mL). After cooling to -20 C, 1,1'-carbonyl-diimidazole (48.84 g, 0.301 mol) was added in portions over 3 h. The flask was equipped with a drying tube filled Drierite. The reaction was warmed to rt over 2 h. After 24 h of vigorous stirring at rt, reaction was cooled to 0 C and methanol (200 mL) was added. The reaction was warmed over 1 h to rt and stirred for an addition 12 h. The contents of the flask were then diluted in EtOAc (200 mL) and filtered with 1:10 MeOH/EtOAc (2 L) through a DCVC column charged with 250 g of Celite (packed at top of column) and 500 g of silica gel (packed at bottom of column). The elutant was concentrated on a rotary evaporator. Recrystallization from a minimal amount hot toluene followed by slow cooling to rt and storage at 4 C for 24 h provided 14.21 g (83%) of methyl ester 50 as a white powder. The remaining mother liquor contained a mixture of 50 and its corresponding acid 49 that could be converted to 50 (1.23 g, 6% yield) by treatment with 0.5 M TMSCH2N2 in THF. This recycled material was not tabulated in the yield. Mp 179-181 C, 1H NMR (500 MHz, CDCl3) delta 8.48 (s, 1H, NH), 7.85 (dd, J = 1.9, 7.4 Hz, 1H); 7.79 (d, J = 1.7 Hz, 1H); 7.77 (dd, J = 1.7, 8.0 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.49 (dd, J = 1.5, 7.5 Hz, 1H), 7.40 (ddd, J = 1.6, 8.3, 11.4 Hz, 1H), 7.39 (ddd, J = 1.6, 8.4, 8.7 Hz, 1H), 3.89 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 170.2. 166.3, 140.1, 137.2, 136.8, 136.0, 133.5, 133.0, 132.5, 132.5, 132.0, 129.6, 127.3, 124.2, 53.1; HREIMS [M+Na]+ m/z: 308.0489 (calcd for C15H11NNaO3S, 308.0357).
  • 4
  • [ 186581-53-3 ]
  • [ 440627-14-5 ]
  • [ 897771-13-0 ]
YieldReaction ConditionsOperation in experiment
86% In methanol; dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere; [000 174] To a stirred solution of 6 (500 mg, 1.84 mmol) in MeOH: CH2C12 (1: 1, 20 mL) under argon atmosphere was added CH2N2 (prepared in situ using N-nitrosomethyl urea (0.95 g, 9.2 mmol) + KOH (0.51 g, 9.22 mmol) at 0 C; warmed to RT and stirred for 1 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 20% EtOAc/ hexanes to afford compound 157 (450 mg, 86%) as white solid. TLC: 30% EtOAc/ hexanes (R 0.5); 1H-NMR (DMSO-d6, 500 MHz): oe 10.82 (s, 1H), 7.82 (s, 1H), 7.75-7.69 (m, 3H), 7.58-7.63 (m, 3H), 3.82 (s, 3H).
  • 5
  • [ 440627-14-5 ]
  • [ 684-93-5 ]
  • [ 897771-13-0 ]
YieldReaction ConditionsOperation in experiment
86% With potassium hydroxide; In methanol; dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere; [00080] To a stirred solution of 27 (500 mg, 1.84 mmol) in MeOH: CH2C12 (1 : 1, 20 mL) under argon atmosphere was added CH2N2 (in situ prepared using N-nitrosomethyl urea (0.95 g, 9.2 mmol) + KOH (0.51 g, 9.22 mmol) at 0 C; warmed to RT and stirred for 1 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 20% EtOAc/ hexanes to afford compound 28 (450 mg, 86%) as white solid. TLC: 30% EtOAc/ hexanes (Rf. 0.5); XH-NMR (DMSO-c, 500 MHz): delta 10.82 (s, 1H), 7.82 (s, 1H), 7.75- 7.69 (m, 3H), 7.58-7.63 (m, 3H), 3.82 (s, 3H).
86% With potassium hydroxide; In methanol; dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere; To a stirred solution of 6 (500 mg, 1.84 mmol) in MeOH: CH2C12 (1: 1, 20 mL) under argon atmosphere was added CH2N2 (in situ prepared using N-nitrosomethyl urea (0.95 g, 9.2 mmol) + KOH (0.51 g, 9.22 mmol) at 0 C; warmed to RT and stirred for 1 h. The reaction wasmonitored by TLC; after completion of the reaction, the volatiles were removed in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 20% EtOAc/ hexanes to afford compound 7 (450 mg, 86%) as white solid. TLC: 30% EtOAc/ hexanes (Rf: 0.5); ?H-NMR (DMSO-d6, 500 MHz): oe 10.82 (s, 1H), 7.82 (s, 1H), 7.75-7.69 (m, 3H), 7.58-7.63 (m, 3H), 3.82 (s, 3H).
 

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