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Chemical Structure| 181696-73-1 Chemical Structure| 181696-73-1

Structure of 181696-73-1

Chemical Structure| 181696-73-1

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Product Details of [ 181696-73-1 ]

CAS No. :181696-73-1
Formula : C16H15NO2
M.W : 253.30
SMILES Code : OC1(C)C(C2=CC=CC=C2)C(C3=CC=CC=C3)=NO1
MDL No. :MFCD08693218
InChI Key :LOFHVOCXHGAVHL-UHFFFAOYSA-N
Pubchem ID :10777254

Safety of [ 181696-73-1 ]

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

Application In Synthesis of [ 181696-73-1 ]

* 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 [ 181696-73-1 ]

[ 181696-73-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 181696-73-1 ]
  • [ 509074-26-4 ]
YieldReaction ConditionsOperation in experiment
13.6 g (79.4 wt%) With chlorosulfonic acid; trifluoroacetic acid; In n-heptane; water; toluene; EXAMPLE 5 Preparation of 4-(5-methyl-3-phenyl-4-isoxazolyl)benzenesulfonyl chloride, 6. 4,5-dihydro-5-methyl-3,4-diphenyl-5-isoxazolol (13.0 grams, 0.0513 mol) was charged to a 200 mL jacketed flask which was cooled with 0.2 C. jacket fluid. Trifluoroacetic acid (9.1 mL, 0.118 mol) was charged to the solids to provide a solution at 38.6 C. The solution was cooled to 2.1 C. and chlorosulfonic acid (34.7 mL, 0.522 mol) was added slowly while maintaining the temperature below 14 C. The solution was heated to 60 C., held for 2.5 hours, cooled to 20 C., and transferred to a 125 mL addition funnel. Toluene (52 mL) and water (52 mL) were charged to the 200 mL jacketed reactor, and cooled to 4 C. The reaction solution was then added slowly to the 200 mL jacketed reactor while maintaining the temperature below 20 C. The multi-phase mixture was warmed to 20 C., and transferred to a 250 mL separatory funnel. Toluene (50 mL) and water (10 mL) were added and the mixture was shaken. Settling of the mixture resulted in two cloudy phases. The toluene phase was washed twice with 15 mL of water, transferred to a 250 mL flask with a 20 mL toluene rinse, and vacuum distilled to 17.4 g of an oil. After initiating crystallization with a glass rod and cooling, heptane (20 mL) was added to the crystalline mass which was broken up to form a powder. The off white powder was collected by filtration. Portions of 50 mL of heptane were used to aid the transfer of solids to the filter. The cake was dried in a vacuum oven (35 C.) to provide 13.6 g (79.4 wt %) of the sulfonyl chloride as an 85:15 mixture of the para and meta isomers. HRMS Calculated for (M+1) C16H13NO3Cl: 334.0305; Found (M+1): 334.0309.
  • 2
  • [ 181696-73-1 ]
  • [3-(5-methyl-3-phenyl-4-isoxazolyl)phenyl]sulfonyl chloride [ No CAS ]
  • [ 509074-26-4 ]
YieldReaction ConditionsOperation in experiment
Example 15: Preparation of 4-(5-methyl-3-phenyl-4- isoxazolyl)benzenesulfonyl chloride (28).; 4,5-Dihydro-5-methyl-3,4-diphenyl-5-isoxazolol 17 (13.0 grams, 0.0513 mol) was charged to a 200 mL jacketed flask which was cooled with 0.2C jacket fluid. Trifluoroacetic acid (9.1 mL, 0.118 mol) was charged to the solids to provide a solution at 38.6C. The solution was cooled to 2.1 C and chlorosulfonic acid (34.7 mL, 0.522 mol) was added slowly while maintaining the temperature below 14C. The solution was heated to 60C, held for 2.5 hours, cooled to 20C, and transferred to a 125 mL addition funnel. Toluene (52 mL) and water (52 mL) were charged to the 200,mL jacketed reactor, and cooled to 4C. The reaction solution was then added slowly to the 200 mL jacketed reactor while maintaining the temperature below 20C. The multi-phase mixture was warmed to 20C, and transferred to a 250 mL separatory funnel. Toluene (50 mL) and water (10 mL) were added and the mixture was shaken. Settling of the mixture resulted in two cloudy phases. The toluene phase was washed twice with 15 mL of water, transferred to a 250 mL flask with a 20 mL toluene rinse, and vacuum distilled to 17.4 g of an oil. After initiating crystallization with a glass rod and cooling, heptane (20 mL) was added to the crystalline mass which was broken up to form a powder. The off white powder was collected by filtration. Portions of 50 mL of heptane were used to aid the transfer of solids to the filter. The cake was dried in a vacuum oven (35C) to provide 13.6 g (79.4 wt% yield of 28) of the sulfonyl chloride as an 85: 15 mixture of the para and meta isomers. HRMS Calculated for (M+1) C16H13NO3Cl: 334.0305; Found (M+1): 334.0309.
 

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