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Chemical Structure| 101349-30-8 Chemical Structure| 101349-30-8

Structure of 101349-30-8

Chemical Structure| 101349-30-8

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Product Details of [ 101349-30-8 ]

CAS No. :101349-30-8
Formula : C9H10ClNO2
M.W : 199.63
SMILES Code : COC(=O)CC1=CC=C(N)C(Cl)=C1
MDL No. :MFCD18398657

Safety of [ 101349-30-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 101349-30-8 ]

* 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 [ 101349-30-8 ]

[ 101349-30-8 ] Synthesis Path-Downstream   1~3

  • 1
  • pyridinium p-toluenesulfonate (PPTS) [ No CAS ]
  • [ 101349-30-8 ]
  • [ 152937-04-7 ]
  • methyl (3-chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% In 5,5-dimethyl-1,3-cyclohexadiene; hexane; ethyl acetate; (Step 2) Synthesis of methyl (3-chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetate In xylene (8 ml), <strong>[152937-04-7]2-bromo-6-fluorobenzothiazole</strong> (330 mg, 1.42 mmol), methyl 4-amino-3-chlorophenylacetate (284 mg, 1.42 mmol), and pyridinium p-toluenesulfonate (PPTS) (107 mg, 0.43 mmol) were heated under reflux for 10 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ ethyl acetate (6:1, v/v) eluate fractions, methyl (3-chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetate (158 mg, 32%) was obtained as a pale yellow solid. 1H-NMR (CDCl3) delta: 3.58 (s, 2H), 3.70 (s, 3H), 7.05-7.10 (m, 1H), 7.22-7.25 (m, 1H), 7.34-7.37 (m, 2H), 7.59-7.63 (m, 1H), 8.32-8.34 (m, 1H). MS (ESI) m/z 351 (M++1).
  • 2
  • [ 79-37-8 ]
  • [ 27018-76-4 ]
  • [ 101349-30-8 ]
  • methyl 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine; In dichloromethane; (Step 3) Synthesis of methyl 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetate To a solution of <strong>[27018-76-4]1-benzylindole-3-carboxylic acid</strong> (201.3 mg, 0.801 mmol) in methylene chloride (4.0 ml) was added oxalyl chloride (103.1 ael, 1.202 mmol) under stirring at -15ØC. The reaction mixture was stirred at room temperature for 2.5 hours and then, distilled under reduced pressure to remove the solvent. The residue was dissolved in methylene chloride (4.0 ml) and to the resulting solution were added a solution of methyl 3-chloro-4-aminophenylacetate (167.9 mg, 0.841 mmol) in methylene chloride (4.0 ml) and triethylamine (0.35 ml, 2.523 mmol) under stirring at room temperature. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was diluted with chloroform, washed with 1N HCl dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby methyl 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetate (341.3 mg, 98%) was obtained. The compound was provided for the subsequent reaction without further purification. 1H-NMR (CDCl3) delta: 3.59 (2H, s), 3.71 (3H, s,), 5.38 (2H, s), 7.08-7.42 (10H, m), 7.87 (1H, s), 8.16 (1H, d, J=7.6Hz), 8.29 (1H, s), 8.58 (1H, d, J=8.0Hz).
  • 3
  • [ 101349-30-8 ]
  • [ 152937-04-7 ]
  • methyl (3-chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridinium p-toluenesulfonate; In 5,5-dimethyl-1,3-cyclohexadiene; for 10.0h; General procedure: A mixture of 2-bromo-6-methylbenzothiazole (15b) (703 mg, 3.08 mmol), methyl 4-amino-3-chlorophenylacetate (16a) (615 mg, 3.08 mmol), and PPTS (232 mg, 0.92 mmol) in xylene (10 ml) was refluxed for 10 h. After cooled to room temperature, the solvent was evaporated. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (6:1, v/v) as eluent to give methyl [3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl]acetate (274 mg, 26%) as a pale yellow oil
 

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