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Chemical Structure| 943443-12-7 Chemical Structure| 943443-12-7

Structure of 943443-12-7

Chemical Structure| 943443-12-7

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Product Details of [ 943443-12-7 ]

CAS No. :943443-12-7
Formula : C7H4ClNO
M.W : 153.57
SMILES Code : ClC1=C2N=COC2=CC=C1
MDL No. :MFCD22988836
InChI Key :QNDGTSQNWUXVEA-UHFFFAOYSA-N
Pubchem ID :22328013

Safety of [ 943443-12-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 943443-12-7 ]

* 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 [ 943443-12-7 ]

[ 943443-12-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 108-86-1 ]
  • [ 943443-12-7 ]
  • [ 943443-18-3 ]
YieldReaction ConditionsOperation in experiment
89% a 500 mL 2-neck round-bottomed flask was equipped with a reflux condenser and replaced by nitrogen. 70 mL of THF that was dried with 0.11 mol of Mg metal was added to the above flask and then, 0.10 mol of 1-bromobenzene was added in a dropwise fashion. The reaction was significantly exodermic and thus a cooling bath was equipped to reduce the temperature inside the reactor less than 50 C. It was agitated for 2 hours at room temperature, 0.11 mol of zinc chloride was added with 100 mL of THF, and further agitated for 2 hours to obtain a slurry-phase reaction mixture. Another flask was replaced by nitrogen and then 0.10 mol of <strong>[943443-12-7]4-chlorobenzo[d]oxazole</strong> derivative, 0.10 mol of Pd, and 3 mol % of Pd(PPh3)4 were dissolved in 100 mL of THF. The prepared solution was added to the reaction mixture and then agitated 60 C. for 24 hours. After the reaction is complete, the resulting product was placed on a silica gel column to remove an inorganic slurry, and then a THF solution was concentrated under vacuum to obtain 4-phenylbenzo[d]oxazole using column chromatography at a yield of 89%.
  • 2
  • [ 106-38-7 ]
  • [ 943443-12-7 ]
  • [ 943443-13-8 ]
YieldReaction ConditionsOperation in experiment
91% a 500 mL 2-neck round-bottomed flask was equipped with a reflux condenser and replaced by nitrogen. 70 mL of THF that was dried with 0.11 mol of Mg metal was added to the above flask and then, 0.10 mol of 1-bromo-4-methylbenzene was added in a dropwise fashion. The reaction was significantly exodermic and thus a cooling bath was equipped to reduce the temperature inside the reactor less than 50 C. It was agitated for 2 hours at room temperature, 0.11 mol of zinc chloride was added with 100 mL of THF, and further agitated for 2 hours to obtain a slurry-phase reaction mixture. Another flask was replaced by nitrogen and then 0.10 mol of <strong>[943443-12-7]4-chlorobenzo[d]oxazole</strong> derivative, 0.10 mol of Pd, and 3 mol % of Pd(PPh3)4 were dissolved in 100 mL of THF. The prepared solution was added to the reaction mixture and then agitated 60 C. for 24 hours. After the reaction is complete, the resulting product was placed on a silica gel column to remove an inorganic slurry, and then a THF solution was concentrated under vacuum to obtain 4-para-tolylbenzo[d]oxazole using column chromatography at a yield of 91%.
  • 3
  • [ 943443-12-7 ]
  • [ 35462-59-0 ]
  • [ 943443-16-1 ]
YieldReaction ConditionsOperation in experiment
91% a 500 mL 2-neck round-bottomed flask was equipped with a reflux condenser and replaced by nitrogen. 70 mL of THF that was dried with 0.11 mol of Mg metal was added to the above flask and then, 1-bromo-4-0.10 mol of (1,1,1,3,3,3-hexafluoropropham-2-yl)benzene was added in a dropwise fashion. The reaction was significantly exodermic and thus a cooling bath was equipped to reduce the temperature inside the reactor less than 50 C. It was agitated for 2 hours at room temperature, 0.11 mol of zinc chloride was added with 100 mL of THF, and further agitated for 2 hours to obtain a slurry-phase reaction mixture. Another flask was replaced by nitrogen and then 0.10 mol of <strong>[943443-12-7]4-chlorobenzo[d]oxazole</strong> derivative, 0.10 mol of Pd, and 3 mol % of Pd(PPh3)4 were dissolved in 100 mL of THF. The prepared solution was added to the reaction mixture and then agitated 60 C. for 24 hours. After the reaction is complete, the resulting product was placed on a silica gel column to remove an inorganic slurry, and then a THF solution was concentrated under vacuum to obtain 4-(4-(1,1,1,3,3,3-hexafluoropropane-2-yl)phenyl)benzo[d]oxazole at a yield of 91% using column chromatography.
  • 4
  • [ 56962-00-6 ]
  • [ 122-51-0 ]
  • [ 943443-12-7 ]
YieldReaction ConditionsOperation in experiment
88% at 105℃; for 4h; Triethyl orthoformate (3 mL) was added to the compound obtained in b) (574 mg, 4 mmol), and the resulting mixture was stirred at 105 C. for 4 hours. The reaction mixture was left to cool to room temperature, and the resulting residue was purified by silica gel column chromatography to obtain crystals of the title compound (538 mg, yield 88%). 1H-NMR (CDCl3) δ: 7.3-7.4 (2H, 7.52 (1H, dd, J=1.4 Hz, 7.8 Hz), 8,15 (1H, s)
  • 5
  • [ 3622-47-7 ]
  • [ 943443-12-7 ]
  • 4-chloro-2-(6-chlorobenzothiazol-2-yl)benzoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With 1,10-Phenanthroline; nickel dichloride; lithium tert-butoxide; In 1,4-dioxane; at 90℃;Inert atmosphere; Under a nitrogen atmosphere, the compound obtained in d) (296 mg, 1.0 mmol), nickel chloride (1.3 mg), 1,10-phenanthroline (1.8 mg), and lithium t-butoxide (160 mg, 2.0 mmol) were added to a solution of the compound obtained in c) (184 mg, 1.2 mmol) in 1,4-dioxane (4 mL), and the resulting mixture was stirred overnight with heating at 90 C. The reaction mixture was left to cool to room temperature, the insoluble matter was removed by using Celite, the filtrate was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain crystals of the title compound (60 mg, yield 19%). 1H-NMR (DMSO-d6) δ: 7.6-7.7 (3H, m), 7.9-8.0 (1H, m), 8.26 (1H, d, J=8.9 Hz), 8.4-8.5 (1H, m)Melting point: 268.2 C.
  • 6
  • [ 943443-12-7 ]
  • ethyl 5-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride [ No CAS ]
  • 5-(benzyloxy)-2-(4-chlorobenzo[d]oxazol-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With benzoic acid; silver carbonate; In acetonitrile; at 60℃; for 8h;Inert atmosphere; Step 1 Ethyl 5-(benzyloxy)-2-(4-chlorobenzo[d]oxazol-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate Under protection of argon gas, ethyl 5-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride 1b (377 mg, 1.0 mmol), <strong>[943443-12-7]4-chlorobenzo[d]oxazole</strong> 7a (184 mg, 1.2 mmol), silver carbonate (330 mg, 1.2 mmol) and benzoic acid (224 mg, 2.0 mmol) were dissolved in 5 mL acetonitrile, and the mixture was reacted at 60 C. for 8 hours. After the reaction was completed, the reaction solution was filtered with celite, the filter cake was washed with ethyl acetate (5 mL), and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: system A) to obtain ethyl 5-(benzyloxy)-2-(4-chlorobenzo[d]oxazol-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 7b (30 mg), yield: 30%. MS m/z(ESI): 493.0 [M+1]
 

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