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[ CAS No. 4755-77-5 ]

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2D
Chemical Structure| 4755-77-5
Chemical Structure| 4755-77-5
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Product Details of [ 4755-77-5 ]

CAS No. :4755-77-5MDL No. :MFCD00000706
Formula : C4H5ClO3 Boiling Point : 135°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :136.53Pubchem ID :20884
Synonyms :

Computed Properties of [ 4755-77-5 ]

TPSA : 43.4 H-Bond Acceptor Count : 3
XLogP3 : 1.4 H-Bond Donor Count : 0
SP3 : 0.50 Rotatable Bond Count : 3

Safety of [ 4755-77-5 ]

Signal Word:DangerClass:8,3
Precautionary Statements:P280-P305+P351+P338-P310UN#:2920
Hazard Statements:H225-H314Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4755-77-5 ]

  • Upstream synthesis route of [ 4755-77-5 ]
  • Downstream synthetic route of [ 4755-77-5 ]

[ 4755-77-5 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 5468-37-1 ]
  • [ 4755-77-5 ]
  • [ 13575-16-1 ]
YieldReaction ConditionsOperation in experiment
22%
Stage #1: With triethylamine In dichloromethane at 0 - 20℃; for 22 h;
Stage #2: for 4 h; Reflux
INTERMEDIATE 51 - PREPARATION OF Ethyl 5-phenyloxazole-2-carboxylate. ; Triethylamine (1.08 mL; 7.69 mmol) was added to a mixture of 2-amino-1-phenylethanone hydrochloride (0.550 g; 3.08 mmol) and ethyl 2-chloro-2-oxoacetate (0.369 mL; 3.23 mmol) in dichloromethane (10 ml.) at 00C. The reaction mixture was then stirred at room temperature for 22 hand diluted with dichloromethane (40 ml_). The organic layer was washed successively with a saturated aqueous solution of sodium carbonate, and water. The organic layer was dried over magnesium sulfate and was concentrated under reduced pressure. The crude residue was dissolved in phosphorus (V) oxychloride (10 ml) and the solution was refluxed for 4 hours. After cooling, the volatiles were removed under reduced pressure and the residue was dissolved in dichloromethane. The organic layer was then carefully washed with a saturated aqueous solution of sodium carbonate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent 15 to 100percent dichloromethane in heptane) to afford 0.146 g (22percent overall yield) of ethyl 5-phenyloxazole-2-carboxylate as a solid. ESI/APCI(+) : 218 (M+H), 240 (M+Na).
Reference: [1] Patent: WO2010/142801, 2010, A1, . Location in patent: Page/Page column 161-162
  • 2
  • [ 4755-77-5 ]
  • [ 15658-60-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 6, p. 1028 - 1030
[2] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 6, p. 1028 - 1030
  • 3
  • [ 4755-77-5 ]
  • [ 15658-60-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 6, p. 1028 - 1030
  • 4
  • [ 4755-77-5 ]
  • [ 118493-85-9 ]
  • [ 40019-21-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 14, p. 3642 - 3657
[2] Patent: WO2007/124546, 2007, A1, . Location in patent: Page/Page column 60
  • 5
  • [ 4755-77-5 ]
  • [ 22059-22-9 ]
  • [ 40019-21-4 ]
YieldReaction ConditionsOperation in experiment
63% With pyridine In dichloromethane for 14 h; Reflux Scheme 11 : Synthesis of ethyl 3-methyl-l,2,4-oxadiazole-5-carboxylate 2.2mTo a solution of (E)-N'-hydroxyacetimidamide 2.0m (1.0 g, 13.50 mmol, 1 eq.) and pyridine (4.35 mL, 54.0 mmol, 4 eq.) in dry DCM (40 mL) was added at RT ethyloxalyl chloride (2.4 g, 18.0 mmol, 1.3 eq.). The solution was stirred at reflux for 14 hours. The reaction mixture was cooled down to RT and quenched with NH4C1 sat. (30 mL). The aqueous phase was extracted with DCM (2 x 50 mL). The organic phases were combined, washed with NaHC03 sat. (50 mL), dried over MgS04, filtered and concentrated under reduced pressure to give 2.2m as yellow oil (1.32 g, 8.45 mmol, 63 percent) which was used in the next step without further purification. LCMS: P = 92 , retention time = 2.0 min, (M+H)+: 157.
Reference: [1] Patent: WO2013/50424, 2013, A1, . Location in patent: Page/Page column 116
  • 6
  • [ 4755-77-5 ]
  • [ 118493-85-9 ]
  • [ 40019-21-4 ]
Reference: [1] Patent: US3991067, 1976, A,
  • 7
  • [ 107-10-8 ]
  • [ 4755-77-5 ]
  • [ 16369-21-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1973, vol. 16, # 6, p. 736 - 739
  • 8
  • [ 623-33-6 ]
  • [ 4755-77-5 ]
  • [ 29655-79-6 ]
YieldReaction ConditionsOperation in experiment
51% With triethylamine In dichloromethane Example 2 Ii; Compound 4 was prepared according to the Ref: J. Hetero. Chem. 1995, 32, 1693-1702. Then, it was reduced by NaBH4ZLiCl in ethanol solution. Further oxidation by Dess-Martin reagent gave the desired aldehyde 6 in 25 percent overall two-step yield.
Reference: [1] Synthetic Communications, 2000, vol. 30, # 17, p. 3171 - 3180
[2] Patent: WO2007/124546, 2007, A1, . Location in patent: Page/Page column 63
[3] Chemische Berichte, 1897, vol. 30, p. 590
[4] Journal of the American Chemical Society, 1997, vol. 119, # 1, p. 86 - 93
[5] Organic Process Research and Development, 2004, vol. 8, # 2, p. 192 - 200
  • 9
  • [ 4755-77-5 ]
  • [ 29655-79-6 ]
Reference: [1] Patent: US2002/35115, 2002, A1,
  • 10
  • [ 4755-77-5 ]
  • [ 108-90-7 ]
  • [ 34966-48-8 ]
YieldReaction ConditionsOperation in experiment
67% With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12 h; Step 1:
Synthesis of ethyl 2-(4-chlorophenyl)-2-oxoacetate
To a stirred solution of chlorobenzene (10 mL, 100.0 mmol) and ethyl 2-chloro-2-oxoacetate (17 mL, 146.0 mmol) in DCM (250 mL) was slowly added aluminum trichloride (25.5 g, 192.0 mmol) at 0° C.
After the addition was completed, the reaction was allowed to warm to room temperature and stir for another 12 h.
The reaction was diluted with EtOAc (500 mL) and washed with water (300 mL) and brine (300 mL).
The organic layer was separated, dried over Na2SO4, filtered and concentrated.
The residue was purified by silica gel column chromatography (PE:EtOAc=10:1 to 5:1) to afford the title compound (14 g, 67percent) as a light oil. MS (ES+) C10H9ClO3 requires: 212, 214. found: 213, 215 [M+H]+.
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 18, p. 6407 - 6415
[2] Patent: US2017/22206, 2017, A1, . Location in patent: Paragraph 0174; 0175; 0176
[3] Journal of Organic Chemistry, 2008, vol. 73, # 10, p. 3842 - 3847
[4] Organic Letters, 2011, vol. 13, # 24, p. 6520 - 6523
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 6, p. 818 - 823
[6] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 8, p. 1958 - 1962
[7] Tetrahedron, 2017, vol. 73, # 39, p. 5813 - 5819
  • 11
  • [ 348-52-7 ]
  • [ 4755-77-5 ]
  • [ 1813-93-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 24, p. 7176 - 7180[2] Angew. Chem., 2018, vol. 130, # 24, p. 7294 - 7298,5
  • 12
  • [ 108-86-1 ]
  • [ 4755-77-5 ]
  • [ 20201-26-7 ]
YieldReaction ConditionsOperation in experiment
60% With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 18 h; [0158] To a stirred mixture ofbromobenzene (0.7 mL, 6.5mmol) and ethyl 2-chloro-2-oxoacetate (0.7 mL, 6.5 mmol)in dichloromethane (12 mL) was added aluminum trichloride(L7 g, 12.5 mmol) at oo C, The reaction was warmed toRTslowly and stirred at RT for 18 h. After poured into cone.hydrochloric acid at oo C, the mixture was extracted withdichloromethane (3x100 mL). The combined organic layerswere washed with brine (100 mL), dried over anhydroussodium sulfate and filtered and concentrated under reducedpressure. The resultant oily matter was purified by silica gelcolunm chromatography (ethyl acetate:petroleum ether=:20) to afford the title compound (1 .0 g, 60percent) as a yellow oiLMS (ES+) C10H9Br03 requires: 256. found: 257, 259[M+Ht.
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 18, p. 6407 - 6415
[2] Tetrahedron Letters, 2006, vol. 47, # 16, p. 2675 - 2678
[3] Chemical Science, 2018, vol. 9, # 48, p. 8930 - 8936
[4] Patent: US2016/31892, 2016, A1, . Location in patent: Paragraph 0156-0158
[5] Journal of Organic Chemistry, 2008, vol. 73, # 10, p. 3842 - 3847
[6] Patent: WO2011/4276, 2011, A1, . Location in patent: Page/Page column 136
[7] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 000697
[8] Tetrahedron, 2017, vol. 73, # 39, p. 5813 - 5819
[9] Patent: WO2006/113471, 2006, A2, . Location in patent: Page/Page column 53
  • 13
  • [ 589-87-7 ]
  • [ 4755-77-5 ]
  • [ 20201-26-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 24, p. 7176 - 7180[2] Angew. Chem., 2018, vol. 130, # 24, p. 7294 - 7298,5
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