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[ CAS No. 119004-72-7 ] {[proInfo.proName]}

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Chemical Structure| 119004-72-7
Chemical Structure| 119004-72-7
Structure of 119004-72-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 119004-72-7 ]

CAS No. :119004-72-7 MDL No. :MFCD01922029
Formula : C16H17NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :287.38 Pubchem ID :-
Synonyms :

Safety of [ 119004-72-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 119004-72-7 ]

* 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 [ 119004-72-7 ]

[ 119004-72-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 4894-75-1 ]
  • [ 105-34-0 ]
  • [ 119004-72-7 ]
YieldReaction ConditionsOperation in experiment
84% With sulfur; diethylamine In methanol at 20℃; for 24h;
61% With sulfur; triethylamine In methanol at 20℃; for 5h; 4 Preparation 4. Methyl 2-amino-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carboxylate A solution of 4-phenylcyclohexanone (CAS: 4894-75-1, 2.00 g, 11.5 mmol), methyl cyanoacetate (CAS: 105-34-0, 1.11 ml, 12.6 mmol), diethylamine (CAS: 109-89-7, 0.59 ml, 5.70 mmol) and sulfur (CAS: 7704-34-9, 121 mg, 3.78 mmol) in methanol (20 ml) was stirred at RT for 5 hours. The reaction was left standing for 16 hours and then the precipitate was collected to afford methyl 2-amino-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate as a white solid mixture (2.00 g, yield 61%).lH NMR (CDCb, 400MHz): d = 7.35 - 7.30 (m, 2H), 7.28 - 7.20 (m, 3H), 5.96 (s, 2H), 3.80 (s, 3H), 3.03 - 2.93 (m, 2H), 2.80 - 2.63 (m, 3H), 2.12 - 2.06 (m, 1H), 1.95 - 1.83 (m, 1H).
With morpholine; sulfur In neat (no solvent) at 75℃; for 1h; General procedure: A mixture of cyclohexanone (0.196 g,2.0 mmol), methyl cyanoacetate (0.198 g, 2.0 mmol),elemental sulfur (0.064 g, 2.0 mmol) and morpholine (0.174g, 2.0 mmol) was heated at 75 °C for 1 h. After nearlycomplete conversion to the corresponding 2-aminothiophene, as was indicated by TLC monitoring, thereaction mixture was cooled to r.t. and the solid residue wasrecrystallized from EtOH to afford methyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (6a). Then asolution of 6a (0.211 g, 1 mmol) in benzonitrile (2 mL) washeated within a flask equipped with an air-filled balloon at200 °C for 24 h in a silicone oil bath. Progress of the reactionwas monitored by TLC. After completion of the reaction, the mixture was cooled to r.t. and the excess of benzonitrile wasremoved under the reduced pressure. The crude product waspurified by column chromatography using n-hexane-EtOAc(8:1) as eluent. The solvent was evaporated under thereduced pressure and the residue was crystallized from nhexane-EtOAc (5:1) to afford the pure product 7a as paleyellow crystals. Yield: 0.188 g, 91%
  • 2
  • [ 27914-73-4 ]
  • [ 119004-72-7 ]
  • methyl 2-(4-hydroxybenzamido)-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 4-acetoxybenzoyl chloride; methyl 2-amino-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Stage #2: With lithium hydroxide monohydrate In tetrahydrofuran; methanol at 40℃; for 0.5h; 18 Example 18. 2-[(4-Hydroxybenzoyl)amino]-6-phenyl-4,5,6,7-tetrahydrobenzothiophene-3- carboxylic acid (Compound 49) To a solution of methyl 2-amino-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (Preparation 4, 1.15 g, 4.00 mmol) in DCM (70 ml) was added DIPEA (CAS: 7087-68-5, 3.50 ml, 20.0 mmol) and 4-acetoxybenzoyl chloride (CAS: 27914-73-4, 953 mg, 4.80 mmol). The reaction mixture was stirred at RT overnight. The reaction was partitioned between DCM and a 0.1M aqueous HC1 solution. The two phases were separated and the organic phase was dried over MgSCL. The solvent was removed under reduced pressure. The residue was suspended in THF (25 ml) and MeOH (25 ml) and LiOH aq. (CAS: 1310-66-3, 0.8M, 336 mg, 8.00 mmol) was added. The reaction was set to stir at RT and next heated at 40 °C for 30 minutes. The reaction was allowed to cool to RT and next acidified to pH ~3 with 1N aqueous HC1 solution. The organic solvents were removed under reduced pressure and the aqueous suspension was filtered to afford methyl 2-(4-hydroxybenzamido)-6-phenyl-4,5,6, 7-tetrahydrobenzo[b] thiophene- 3 -carboxy late as a white solid (1.60 g, yield 98%). Methyl 2-(4-hydroxybenzamido)-6-phenyl-4, 5,6,7- tetrahydrobenzo[b]thiophene-3-carboxylate was finally hydrolysed to give 2-[(4- hydroxybenzoyl)amino]-6-phenyl-4,5,6, 7-tetrahydrobenzothiophene-3-carboxylic acid according to the procedure described in Example 10 (white solid, yield 96%).1H NMR (DMSO-de, 400MHz): d = 13.27 (s, 1H), 12.32 (s, 1H), 10.42 (s, 1H), 7.80 - 7.75 (m, 2H), 7.35 - 7.29 (m, 4H), 7.26 - 7.20 (m, 1H), 6.98 - 6.93 (m, 2H), 3.06 - 2.88 (m, 3H), 2.76 (dd, J=l l.0, 14.2 Hz, 2H), 2.02 (d, J=l l.O Hz, 1H), 1.94 - 1.84 (m, 1H). LC/MS (Table 1, Method A) Rt= 5.07 min; MS ra/z: 394 [M+H]+.
  • 3
  • [ 4894-75-1 ]
  • [ 105-56-6 ]
  • [ 119004-72-7 ]
YieldReaction ConditionsOperation in experiment
62% With sulfur; triethylamine In ethanol at 70℃; for 2h; Inert atmosphere; 4.1.2. General Procedure A for the Synthesis of Compounds (4a-4p) General procedure: To a suspension of malonitrile or cyanoacetate (methyl/ethyl/t-butylcyanoacetate) (5 mmol),the appropriate ketone corresponding to 4-methyl/phenylcyclohexanone, N-acetyl-4-piperidone or methoxy/ethoxycarbonyl-4-piperidone (5 mmol), TEA (0.44 mL, 5 mmol) and sulfur (164 mg, 5 mmol)in the appropriate solvent (methanol or ethanol, 10 mL) was stirred for 2 h at 70 C. The solvent wasevaporated, and the residue was diluted with dichloromethane (15 mL). After washing with water(2 5 mL) and brine (5 mL), the organic layer was dried over anhydrous Na2SO4 and evaporated.The crude product was purified by column chromatography on silica gel or by crystallization fromethyl ether.
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