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Chemical Structure| 35444-47-4 Chemical Structure| 35444-47-4

Structure of 35444-47-4

Chemical Structure| 35444-47-4

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Product Details of [ 35444-47-4 ]

CAS No. :35444-47-4
Formula : C8H13ClO3
M.W : 192.64
SMILES Code : O=C(OC)CCCCCC(Cl)=O
MDL No. :N/A

Safety of [ 35444-47-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 35444-47-4 ]

* 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 [ 35444-47-4 ]

[ 35444-47-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 20291-40-1 ]
  • [ 35444-47-4 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 1h;Reflux; General procedure: A soln of 4a (1.46 g, 10 mmol) in SOCl2 (4 ml) was refluxed for 1 h. The SOCl2 was removed under reduced pressure to afford an orange oil, which was added dropwise to a stirred solution of 2a (1.42 g, 8 mmol) and Et3N (3.5 ml, 25 mmol) in anhydrous tetrahydrofuran (65 ml) at 0 C. The reaction mixture was allowed to be stirred overnight at room temperature. The solvent was removed in vacuum and the residue was diluted with dichloromethane (150 ml), washed with 1 M H3PO4 (3 × 80 ml) and brine (3 × 80 ml) and dried over with MgSO4. Filtration and concentration in vacuum and recrystallization from AcOEt gave 1.29 g of 5a as a white crystal.
With thionyl chloride; In benzene; for 3h;Reflux; General procedure: A solution of monomethyl alkanoic acid (n = 3-7) (1.2 eq) and thionyl chloride (1.4 eq) in benzene (5 mL) was refluxed for 3 h. Subsequently, the majority of the SOCl2 and benzene were removed by distillation. The mixture was cooled down to room temperature and dried under a vacuum to give a crude chlorocarbonyl-alkanoic acid methyl ester. A solution of chlorocarbonyl-alkanonic acid methyl ester in dichloromethane (5 mL) was added to a round flask containing 14 (1 eq) by cannula, and subsequently added pyridine (3.5 eq). The resulting solution was stirred at room temperature overnight, and quenched by adding water. The solution was extracted with ethyl acetate, dried (MgSO4), and evaporated to give a residue which was purified by column chromatography (Al2O3), eluting by ethyl acetate /hexane (1:15) to provide 15-19.
With thionyl chloride; for 2h;Reflux; 5.1.3 Methyl 7-((5-(4-morpholinophenyl)-1,3,4-thiadiazol-2-yl)amino)-7-oxoheptanoate (86) A soln of 84 (1.74 g, 10 mmol) in SOCl2 (4 ml) was refluxed for 2 h. The removal of SOCl2 under reduced pressure yielded orange oil, which was dissolved in dichloromethane.
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 4h; General procedure: The oxalyl chloride (0.91 mL, 10.8 mmol) was added into thesolution of methyl 8-chloro-8-oxooctanoate (9, 680 mg, 3.6 mmol)and dry DMF (0.15 mL) in dry DCM (20 mL), then the mixturestirred at room temperature for 4 h. The excess oxalyl chloride andsolvent were evaporated under vacuum. The crude product (10) ofmonomethyl acid chloride was directly used for further reactionwithout any purification.

  • 2
  • [ 828-81-9 ]
  • [ 35444-47-4 ]
  • methyl 7-((5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)amino)-7-oxoheptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; General procedure: 5.1.3 Methyl 7-((5-(4-morpholinophenyl)-1,3,4-thiadiazol-2-yl)amino)-7-oxoheptanoate (86) A soln of 84 (1.74 g, 10 mmol) in SOCl2 (4 ml) was refluxed for 2 h. The removal of SOCl2 under reduced pressure yielded orange oil, which was dissolved in dichloromethane. The resulting solution was added dropwise to a solution of 59 (1.71 g, 6.5 mmol) and Et3N (3.5 mL, 25 mmol) in dichloromethane (130 mL) at 0 C. The resulting reaction mixture was stirred overnight at room temperature, washed by 1 M H3PO4 (3 * 80 mL) and brine (3 * 80 mL), and dried (MgSO4). Concentration and recrystallization from EtOAc gave 0.98 g of compound 86 as a colorless crystal. Yield: 36%; The synthetic procedures of compounds 87-119 were the same as that described above. 5.1.3.9 Methyl 7-((5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)amino)-7-oxoheptanoate (95) Yield: 67%, mp: 155-157 C (EtOAc). ESI-MS m/z: 368.2 [M+H]+; 1H NMR (CDCl3) delta 1.45-1.55 (m, 2H), 1.66-1.76 (m, 2H), 1.82-1.92 (m, 2H), 2.32 (t, J = 7.2 Hz, 2H), 2.84 (t, J = 7.2 Hz, 2H), 3.63 (s, 3H), 7.40-7.46 (m, 2H), 7.51-7.57 (m, 1H), 8.14-8.19 (m, 1H), 13.17 (s, 1H).
  • 3
  • [ 828-81-9 ]
  • [ 35444-47-4 ]
  • N<SUP>1</SUP>-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)-N<SUP>7</SUP>-hydroxyheptanediamide [ No CAS ]
 

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