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Chemical Structure| 21900-30-1 Chemical Structure| 21900-30-1

Structure of 21900-30-1

Chemical Structure| 21900-30-1

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Product Details of [ 21900-30-1 ]

CAS No. :21900-30-1
Formula : C8H6Cl2O
M.W : 189.04
SMILES Code : O=C(Cl)C1=CC=C(C)C(Cl)=C1
MDL No. :MFCD07787492

Safety of [ 21900-30-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 21900-30-1 ]

* 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 [ 21900-30-1 ]

[ 21900-30-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 5162-82-3 ]
  • [ 21900-30-1 ]
  • 2
  • [ 5162-82-3 ]
  • [ 21900-30-1 ]
  • [ 109-89-7 ]
  • [ 97712-32-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; N-methyl-acetamide; thionyl chloride; water; ethyl acetate; EXAMPLE 1 Preparation of 3-chloro-N,N-diethyl-p-toluamide STR47 A mixture of 32.2 g (0.19 mol) of <strong>[5162-82-3]3-chloro-4-methylbenzoic acid</strong> in 100 mL of thionyl chloride is treated with 2 drops of dimethylformamide and heated on a steam bath for one hour. The clear amber solution is evaporated in vacuo several times with anhydrous toluene to give a clear amber oily residue. After dilution to a volume of 125 mL with anhydrous tetrahydrofuran, the 3-chloro-4-methyl-benzoyl chloride is added dropwise to a stirred solution of 43.3 mL (0.418 mol) of diethylamine in 300 mL anhydrous tetrahydrofuran under N2 at -5 C. The reaction mixture is allowed to come to room temperature over a 72 hour period then is treated with 300 mL water. The phases are separated; the aqueous phase is extracted with a total of 300 mL ethyl acetate. All organic phases are combined, washed with 300 mL of a saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo to give 40.0 g of a clear dark red oil. The infrared and proton nmr spectra are consistent with the desired structure. Gas-liquid chromatography analysis gives a purity of 96%.
In tetrahydrofuran; N-methyl-acetamide; thionyl chloride; water; ethyl acetate; EXAMPLE 1 Preparation of 3-chloro-N,N-diethyl-p-toluamide STR12 A mixture of 32.2 g (0.19 mol) of <strong>[5162-82-3]3-chloro-4-methylbenzoic acid</strong> in 100 mL of thionyl chloride is treated with 2 drops of dimethylformamide and heated on a steam bath for one hour. The clear amber solution is evaporated in vacuo several times with anhydrous toluene to give a clear amber oily residue. After dilution to a volume of 125 mL with anhydrous tetrahydrofuran, the 3-chloro-4-methyl-benzoyl chloride is added dropwise to a stirred solution of 43.3 mL (0.418 mol) of diethylamine in 300 mL anhydrous tetrahydrofuran under N2 at -5 C. The reaction mixture is allowed to come to room temperature over a 72 hour period then is treated with 300 mL water. The phases are separated; the aqueous phase is extracted with a total of 300 mL ethyl acetate. All organic phases are combined, washed with 300 ml of a saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo to give 40.0 g of a clear dark red oil. The infrared and proton nmr spectra are consistent with the desired structure. Gas-liquid chromatography analysis gives a purity of 96%.
  • 3
  • [ 626-23-3 ]
  • [ 5162-82-3 ]
  • [ 21900-30-1 ]
  • [ 27922-74-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In C6; thionyl chloride; benzene; Preparation of 3-chloro,4-methyl-N,N-di-sec.butyl-benzamide Into a 150 ml flask, provided with a reflux condenser, were placed 17.1 g of <strong>[5162-82-3]3-chloro-4-methyl-benzoic acid</strong> (prepared according to French Pat. No. 835,727) and 55.5 g of SOCl2 and the whole was heated to reflux until complete dissolution. The boiling was continued for another 30 minutes. The excess in SOCl2 was then removed under vacuum and the residue was subjected to fractional distillation at a pressure of 0.2 mm Hg. The fraction passing over at 95C was then collected. 17.9 g of the chloride of 3-chloro,4-methylbenzoic acid were obtained. To these 17.9 g of the chloride of 3-chloro,4-methylbenzoic acid, dissolved in 60 ml of anhydrous benzene, were added 12.9 g of di-sec.butylamine dissolved in 15 ml of anhydrous C6 H 6 and 12.3 g of triethylamine. The whole was then boiled to reflux temperature for 1 hour and was then left to cool down to room temperature. The reaction mass was then concentrated to dryness under reduced pressure. The residue was washed with acidulated H2 O, with H2 O and extracted with ethyl ether. The etheral extract was dried on anhydrous Na 2 SO4, filtered, and the solvent was then removed by reduced pressure. The oily residue was fractionally distilled at a pressure of 0.05 mm Hg. The fraction which passed over at 143-144C was collected. Thereby were obtained 26.5 g of 3-chloro,4-methyl-N,N-di-sec.butyl-benzamide. The analysis gave: calculated C = 68.19%, found C = 64.93%; calculated H = 8.55%, found H = 8.83%.
 

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