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Chemical Structure| 56762-32-4
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Product Details of [ 56762-32-4 ]

CAS No. :56762-32-4 MDL No. :MFCD11113372
Formula : C8H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :RVYRSQRMEZKASP-UHFFFAOYSA-N
M.W : 169.61 Pubchem ID :23380945
Synonyms :

Safety of [ 56762-32-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 56762-32-4 ]

* 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.

  • Upstream synthesis route of [ 56762-32-4 ]
  • Downstream synthetic route of [ 56762-32-4 ]

[ 56762-32-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 7137-38-4 ]
  • [ 56762-32-4 ]
YieldReaction ConditionsOperation in experiment
59.1% at 20 - 50℃; for 12 h; Synthesis of 2,8-Dichloro-4-methyl-quinazoline  To a solution of the compound 11 (3.0g, 0.014 mol) in 20 mL of anhydrous CH2CI2 was added SOCI2 (8.9 g, 0.069 mol) and DMF (one drop), then themixture was heated to reflux for 2 hours. The resulting mixture wasconcentrated in vacuum to give compound 11a (3.1 g, yield: 95.4percent) as a yellow solid, which was used for next step withoutfurther purification.To a solution of Mg (0.4 g, 0.017mol) in 30 mL of anhydrous THF was added EtOH (1 .278 g, 0.028 mol) and CCI4 (0.1 mL) at 50°C. After being stirred for 30min, a solution of diethyl malonate (2.6 g,0.017 mol) and EtOH (0.89 g, 0.019 mol) in 10mL of anhydrous THF was added, the mixture was stirred at 60°C for 2 hours. Tothis solution was added a solution ofcompound 11a (3.1 g, 0.014 mol) in 10 mL ofTHF, the mixture was stirred at 60°C for 1 hour. The reaction mixture was cooledand quenched with 10 ml of aqueous H2SO4 (10 percent), the organic layers were concentrated invacuum to give an yellow oil. To this oil was added amixture of CH3COOH (15 mL), H2SO4 (2 mL) and H2O (10 mL),the mixture was stirred at reflux for 10hours. The resulting mixture was extracted with EtOAc (50 mL χ 3), the organic layers were concentrated invacuum to afford compound 11 b (2.4 g, yield: 86.5percent).To a solution of the compound 11 b(2.0 g, 10 mmol) in 15 mL of HOAc was addedFe (1 .68g, 30.0 mmol), the mixture was stirred at room temperature for 4 hoursand then at 50°C for 8 hours. The solution was cooled and made alkaline byaddition of 10 percent aqueous NaOH solution,extracted with EtOAc (10 mL x 3), theorganic layers were concentrated in vacuum to afford compound 11d (0.998 g,yield: 59.1 percent).To a solution of the compound 11d(0.8 g, 4.7 mmol) in 10 mL of THF was addedDMAP (0.564 g, 5.64mmol) and CI3CCOCI (0.855 mg, 4.7 mmol ) at 0°C, then themixture was stirred at room temperature for 6 hours. The resulting mixture wasdiluted with ice water (50 mL), extracted with EtOAc (5 mL x 3), the organiclayers were concentrated in vacuum to give compound 11e (0.970 g, yield:65.8percent), which was used for next step without further purification.To a solution of the compound 11e(0.9 g, 2.87 mmol) in 5 mL of DMSO was added CH3COONH4 (1 .107 g, 14.4 mmol), themixture was stirred at room temperature for 20 hours. The resulting mixture wasdiluted with cold water, the formed precipitate was collected by filtration anddried under vacuum to afford compound 8-chloro-4-methyl-1 H-quinazolin-2-one(0.373 g, yield: 67percent), which was used for next step without furtherpurification.To a solution of the compound8-chloro-4-methyl-1 H-quinazolin-2-one (200 mg, 1 .12 mmol) in 15 mL of toluenewas added POCI3 (350 mg, 2.25 mmol) and DIPEA (270 mg, 2.25 mmol), then themixture was stirred at 120°C for 4 hours. The resulting mixture wasconcentrated in vacuum, the residue was washed with Et2O (25 mL χ 3) to give2,8-Dichloro-4-methyl-quinazoline (150 mg, yield: 68.2percent). m/z = 197 [M + H]+
Reference: [1] Patent: WO2013/50527, 2013, A1, . Location in patent: Page/Page column 55; 56; 57
  • 2
  • [ 75-16-1 ]
  • [ 56762-32-4 ]
YieldReaction ConditionsOperation in experiment
51.4% at 0℃; for 2 h; Step 2: Compound 151-3 (26 g, 0.12 mol) was dissolved in THF (300 mL), MeMgBr (120 mL, 3M in Et2O) wasadded slowly into the solution at 0 °C. After the addition, the reaction mixture was kept at 0°C for 2h, and then pouredinto ammonium chloride aqueous solution, extracted with EtOAc, the extraction liquid was washed with brines, driedover anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by column chromatographyto deliver compound 151-4 (10.5 g, yield 51.4percent) as yellow solid. MS ESI calcd for C8H8CNO [M+H]+ 169, found 169.
Reference: [1] Patent: EP3124482, 2017, A1, . Location in patent: Paragraph 0319; 0320
  • 3
  • [ 533-17-5 ]
  • [ 56762-32-4 ]
Reference: [1] Photochemical and Photobiological Sciences, 2016, vol. 15, # 1, p. 105 - 116
  • 4
  • [ 533-17-5 ]
  • [ 6953-83-9 ]
  • [ 56762-32-4 ]
Reference: [1] Photochemical and Photobiological Sciences, 2016, vol. 15, # 1, p. 105 - 116
  • 5
  • [ 676-58-4 ]
  • [ 53312-77-9 ]
  • [ 56762-32-4 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 13, p. 4052 - 4056
  • 6
  • [ 533-17-5 ]
  • [ 6953-83-9 ]
  • [ 56762-32-4 ]
  • [ 95-51-2 ]
Reference: [1] Photochemical and Photobiological Sciences, 2016, vol. 15, # 1, p. 105 - 116
  • 7
  • [ 4771-47-5 ]
  • [ 56762-32-4 ]
Reference: [1] Patent: WO2013/50527, 2013, A1,
  • 8
  • [ 19088-99-4 ]
  • [ 56762-32-4 ]
Reference: [1] Patent: WO2013/50527, 2013, A1,
  • 9
  • [ 95-51-2 ]
  • [ 56762-32-4 ]
Reference: [1] Photochemical and Photobiological Sciences, 2016, vol. 15, # 1, p. 105 - 116
  • 10
  • [ 6388-47-2 ]
  • [ 56762-32-4 ]
Reference: [1] Patent: EP3124482, 2017, A1,
  • 11
  • [ 95-51-2 ]
  • [ 6953-83-9 ]
  • [ 56762-32-4 ]
Reference: [1] Photochemical and Photobiological Sciences, 2016, vol. 15, # 1, p. 105 - 116
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