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[ CAS No. 393-52-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 393-52-2
Chemical Structure| 393-52-2
Chemical Structure| 393-52-2
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Product Details of [ 393-52-2 ]

CAS No. :393-52-2 MDL No. :MFCD00000656
Formula : C7H4ClFO Boiling Point : -
Linear Structure Formula :- InChI Key :RAAGZOYMEQDCTD-UHFFFAOYSA-N
M.W : 158.56 Pubchem ID :9808
Synonyms :

Calculated chemistry of [ 393-52-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.58
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 2.75
Log Po/w (WLOGP) : 2.62
Log Po/w (MLOGP) : 2.48
Log Po/w (SILICOS-IT) : 2.76
Consensus Log Po/w : 2.45

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.185 mg/ml ; 0.00117 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.273 mg/ml ; 0.00172 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.0938 mg/ml ; 0.000592 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 393-52-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P390-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 UN#:3265
Hazard Statements:H314-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 393-52-2 ]

* 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 [ 393-52-2 ]
  • Downstream synthetic route of [ 393-52-2 ]

[ 393-52-2 ] Synthesis Path-Upstream   1~35

  • 1
  • [ 393-52-2 ]
  • [ 1006-19-5 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 257 - 264
  • 2
  • [ 445-29-4 ]
  • [ 393-52-2 ]
YieldReaction ConditionsOperation in experiment
70% With thionyl chloride In toluene at 50℃; for 7 h; Reflux Step I
2-fluorobenzoyl chloride (Intermediate a)
To 100mL of toluene were added 0.714 mol of 2-fluorobenzoic acid (100 g) then the mixture was heated to 50°C and added 5.7 mol (414mL) sulfoxide chloride .The reaction mixture was refluxed for 7 h.
After completion of the reaction, sulfoxide chloride was evaporated to give 2-fluorobenzoyl chloride 79 g. Yield: 70percent.
70% With thionyl chloride In toluene at 50℃; for 7 h; To 100 mL of toluene were added 0.714 mol of 2-fluorobenzoic acid (100 g) then the mixture was heated to 50° C. and added 5.7 mol (414 mL) sulfoxide chloride.
The reaction mixture was refluxed for 7 h.
After completion of the reaction, sulfoxide chloride was evaporated to give 2-fluorobenzoyl chloride 79 g. Yield: 70percent.
Reference: [1] Phosphorus, Sulfur and Silicon and Related Elements, 1996, vol. 113, # 1-4, p. 179 - 207
[2] Journal of Organometallic Chemistry, 2005, vol. 690, # 17, p. 3918 - 3928
[3] Organic and Biomolecular Chemistry, 2009, vol. 7, # 23, p. 4886 - 4894
[4] Patent: EP2799437, 2014, A1, . Location in patent: Paragraph 0055
[5] Patent: US2014/364431, 2014, A1, . Location in patent: Paragraph 0186
[6] Russian Journal of Organic Chemistry, 2010, vol. 46, # 3, p. 318 - 321
[7] Zeitschrift fuer Physikalische Chemie (Leipzig), 1930, vol. <B> 10, p. 106,119
[8] Chemische Berichte, 1931, vol. 64, p. 1455,1480[9] Chemische Berichte, 1933, vol. 66, p. 286,291
[10] Nippon Kagaku Zasshi, 1958, vol. 79, p. 1428,1430[11] Chem.Abstr., 1960, p. 5518
[12] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 257 - 264
[13] Journal of Medicinal Chemistry, 1983, vol. 26, # 5, p. 765 - 768
[14] Magnetic Resonance in Chemistry, 1993, vol. 31, # 9, p. 836 - 840
[15] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4512 - 4516
[16] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 202 - 211
[17] Synthesis, 1996, # 4, p. 514 - 518
[18] Journal of Heterocyclic Chemistry, 1998, vol. 35, # 1, p. 225 - 229
[19] Journal of Medicinal Chemistry, 1999, vol. 42, # 6, p. 981 - 991
[20] Pesticide Science, 1994, vol. 41, # 2, p. 139 - 148
[21] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 1, p. 21 - 31
[22] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 2, p. 171 - 175
[23] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 12, p. 3933 - 3939
[24] Organic Letters, 2003, vol. 5, # 25, p. 4795 - 4798
[25] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10195 - 10198
[26] Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 839 - 848
[27] European Journal of Medicinal Chemistry, 2006, vol. 41, # 12, p. 1421 - 1429
[28] Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1365 - 1379
[29] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 8, p. 4233 - 4241
[30] Journal of Organometallic Chemistry, 2008, vol. 693, # 18, p. 3081 - 3091
[31] Journal of Medicinal Chemistry, 2009, vol. 52, # 4, p. 1115 - 1125
[32] Patent: US2005/239767, 2005, A1, . Location in patent: Page/Page column 10
[33] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5716 - 5721
[34] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 13, p. 3936 - 3940
[35] Letters in Drug Design and Discovery, 2010, vol. 7, # 3, p. 188 - 193
[36] Journal of Fluorine Chemistry, 2009, vol. 130, # 11, p. 1028 - 1034
[37] Journal of Medicinal Chemistry, 2010, vol. 53, # 19, p. 7011 - 7020
[38] Chemical Biology and Drug Design, 2010, vol. 75, # 5, p. 489 - 493
[39] Synthesis, 2010, # 24, p. 4273 - 4281
[40] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 6, p. 481 - 484
[41] Medicinal Chemistry, 2010, vol. 6, # 4, p. 211 - 218
[42] Angewandte Chemie - International Edition, 2011, vol. 50, # 39, p. 9081 - 9084
[43] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 3551 - 3563
[44] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3170 - 3181
[45] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4189 - 4204
[46] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 12, p. 3915 - 3924
[47] Synthetic Communications, 2012, vol. 42, # 23, p. 3524 - 3531
[48] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2843 - 2855
[49] Chemical Communications, 2013, vol. 49, # 46, p. 5313 - 5315
[50] Chemistry--A European Journal, 2015, vol. 21, # 1, p. 205 - 209
[51] Archiv der Pharmazie, 2013, vol. 346, # 7, p. 521 - 533
[52] Patent: EP2647622, 2013, A1, . Location in patent: Paragraph 0124
[53] Patent: US2013/317110, 2013, A1, . Location in patent: Paragraph 0139
[54] Bioorganic Chemistry, 2014, vol. 52, p. 1 - 7
[55] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 192 - 194
[56] Organic Letters, 2014, vol. 16, # 2, p. 390 - 393
[57] Molecules, 2013, vol. 18, # 12, p. 15737 - 15749
[58] Letters in Drug Design and Discovery, 2015, vol. 12, # 6, p. 488 - 494
[59] Chemistry - A European Journal, 2014, vol. 20, # 31, p. 9739 - 9743
[60] Patent: WO2014/125506, 2014, A2, . Location in patent: Page/Page column 21
[61] Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 2, p. 449 - 455
[62] Journal of Fluorescence, 2014, vol. 24, # 4, p. 995 - 1001
[63] Turkish Journal of Chemistry, 2013, vol. 37, # 6, p. 909 - 916
[64] Journal of the American Chemical Society, 2014, vol. 136, # 33, p. 11590 - 11593
[65] Chemical Communications, 2014, vol. 50, # 77, p. 11303 - 11306
[66] Chemical Communications, 2015, vol. 51, # 1, p. 77 - 80
[67] Organic Letters, 2014, vol. 16, # 24, p. 6412 - 6415
[68] Organic Letters, 2015, vol. 17, # 5, p. 1228 - 1231
[69] European Journal of Medicinal Chemistry, 2015, vol. 90, p. 436 - 447
[70] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9364 - 9368
[71] European Journal of Medicinal Chemistry, 2014, vol. 90, p. 436 - 447
[72] Science China Chemistry, 2015, vol. 58, # 8, p. 1302 - 1309
[73] Synlett, 2015, vol. 26, # 11, p. 1455 - 1460
[74] Chinese Chemical Letters, 2016, vol. 27, # 1, p. 163 - 167
[75] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1484 - 1488
[76] Journal of Molecular Structure, 2016, vol. 1117, p. 8 - 16
[77] Organic Letters, 2014, vol. 16, # 21, p. 5644 - 5647
[78] Journal of Organic Chemistry, 2016, vol. 81, # 8, p. 3416 - 3422
[79] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2544 - 2546
[80] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3263 - 3270
[81] Chemical Communications, 2016, vol. 52, # 70, p. 10676 - 10679
[82] Chinese Chemical Letters, 2016, vol. 27, # 9, p. 1547 - 1550
[83] Pharmacological Research, 2016, vol. 113, p. 610 - 625
[84] Chemical Biology and Drug Design, 2016, p. 664 - 676
[85] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5372 - 5376
[86] Molecules, 2016, vol. 21, # 11,
[87] Organic Letters, 2016, vol. 18, # 21, p. 5536 - 5539
[88] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 3, p. 393 - 397
[89] Tetrahedron, 2017, vol. 73, # 12, p. 1576 - 1582
[90] Journal of Organic Chemistry, 2017, vol. 82, # 6, p. 3245 - 3251
[91] Chemistry - A European Journal, 2017, vol. 23, # 15, p. 3577 - 3582
[92] Patent: WO2017/37672, 2017, A1, . Location in patent: Page/Page column 49; 50
[93] Journal of Molecular Structure, 2017, vol. 1138, p. 177 - 191
[94] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 420 - 430
[95] Chemical Communications, 2017, vol. 53, # 33, p. 4601 - 4604
[96] Organic Letters, 2017, vol. 19, # 10, p. 2746 - 2749
[97] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 11, p. 2641 - 2644
[98] Synthesis (Germany), 2017, vol. 49, # 13, p. 2865 - 2872
[99] Journal of Medicinal Chemistry, 2017, vol. 60, # 15, p. 6622 - 6637
[100] Synthesis (Germany), 2017, vol. 49, # 17, p. 3937 - 3944
[101] Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2360 - 2364
[102] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1740 - 1750
[103] Medicinal Chemistry Research, 2018, vol. 27, # 5, p. 1528 - 1537
[104] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 197 - 209
[105] RSC Advances, 2018, vol. 8, # 50, p. 28668 - 28675
[106] Journal of Medicinal Chemistry, 2018, vol. 61, # 15, p. 6609 - 6628
[107] Chemical Communications, 2018, vol. 54, # 77, p. 10859 - 10862
[108] Patent: US4022900, 1977, A,
  • 3
  • [ 320-11-6 ]
  • [ 393-52-2 ]
YieldReaction ConditionsOperation in experiment
98% at 125 - 130℃; for 1 h; (2) taking 2.97 mol of o-chlorotrichlorobenzene obtained in step (1)Stirring up to 125 ~ 130 ,Keep micro negative pressure,The micro-negative pressure is 0 to 0.5 cm water column,Began to slowly drop 0.5percent zinc chloride aqueous solution,3 hours drop finished,Maintaining the reaction temperature 125 to 130 ° C,Insulation for 1 hour,GC tracking reaction process,If the o-fluoro-trichloro Bian complement the incomplete conversion zinc chloride solution dropwise until complete conversion of o-fluoro-trichloro Bian,Using vacuum distillation method of purification,Collecting 100 to 105 ° C fractions,The product was o-fluorobenzoyl chloride 416.6 g,Purity 99.5percent yield 98percent.
Reference: [1] Patent: CN106008197, 2016, A, . Location in patent: Paragraph 00119; 0020
  • 4
  • [ 445-29-4 ]
  • [ 393-52-2 ]
Reference: [1] Patent: US4999356, 1991, A,
  • 5
  • [ 445-29-4 ]
  • [ 393-52-2 ]
Reference: [1] Patent: US4999356, 1991, A,
  • 6
  • [ 445-29-4 ]
  • [ 393-52-2 ]
Reference: [1] Patent: US4195023, 1980, A,
  • 7
  • [ 10026-13-8 ]
  • [ 108-95-2 ]
  • [ 445-29-4 ]
  • [ 393-52-2 ]
Reference: [1] Patent: US4999356, 1991, A,
  • 8
  • [ 10026-13-8 ]
  • [ 108-95-2 ]
  • [ 445-29-4 ]
  • [ 393-52-2 ]
Reference: [1] Patent: US4999356, 1991, A,
  • 9
  • [ 69038-73-9 ]
  • [ 393-52-2 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 6, p. 3245 - 3251
  • 10
  • [ 3416-93-1 ]
  • [ 445-29-4 ]
  • [ 393-52-2 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 9, p. 3354 - 3357
  • 11
  • [ 79-37-8 ]
  • [ 445-29-4 ]
  • [ 393-52-2 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12149 - 12152
  • 12
  • [ 106-47-8 ]
  • [ 393-52-2 ]
  • [ 784-38-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 3, p. 663 - 669
[2] Synthetic Communications, 2012, vol. 42, # 1, p. 46 - 54
  • 13
  • [ 393-52-2 ]
  • [ 2886-65-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 3, p. 663 - 669
  • 14
  • [ 696-62-8 ]
  • [ 393-52-2 ]
  • [ 348-52-7 ]
  • [ 100-07-2 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10140 - 10144
  • 15
  • [ 393-52-2 ]
  • [ 446-24-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2005, vol. 41, # 12, p. 1511 - 1520
[2] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 257 - 264
[3] Chemische Berichte, 1937, vol. 70, p. 1416,1419
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 192 - 194
[5] Journal of Fluorescence, 2014, vol. 24, # 4, p. 995 - 1001
[6] Journal of Molecular Structure, 2016, vol. 1117, p. 8 - 16
[7] Journal of Molecular Structure, 2017, vol. 1138, p. 177 - 191
  • 16
  • [ 393-52-2 ]
  • [ 443-26-5 ]
Reference: [1] Patent: US4801717, 1989, A,
  • 17
  • [ 64-17-5 ]
  • [ 393-52-2 ]
  • [ 443-26-5 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 22, p. 7557 - 7576
[2] Journal of Organic Chemistry, 2008, vol. 73, # 24, p. 9781 - 9783
  • 18
  • [ 393-52-2 ]
  • [ 80277-41-4 ]
YieldReaction ConditionsOperation in experiment
66% With sodium iodide In dichloromethane; acetonitrile STR22
The reaction was carried out under Argon. Cuprous cyanide (4.67 g, 52.2 mmol) and anhydrous sodium iodide (14.61 g, 97 mmol) were stirred for 2 minutes in anhydrous acetonitrile (100 ml).
The resulting solution was mixed with o-fluoro benzoyl chloride (7.73 g, 48.7 mmol) whereupon an orange precipitate formed.
The mixture was stirred for 30 minutes at room temperature, filtered and concentrated in vacuo.
The residue was taken up in dichloromethane and the resultant precipitate was filtered off.
Concentration of the filtrate under reduced pressure gave an orange oil.
Distillation in Kugelror apparatus gave o-fluorobenzoyl cyanide as a yellow liquid (5.07 g, 66percent).
NMR (60 MHz, CDCl3): δ 7.2-8.2 (4H, complex).
IR (liquid film): 2225 (medium), 1680 (strong), 1610 (strong), 1580 (medium), 750 (strong) cm-1.
Reference: [1] Patent: US4912262, 1990, A,
[2] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 680 - 687
  • 19
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  • [ 393-52-2 ]
  • [ 80277-41-4 ]
Reference: [1] Synthesis, 1983, # 8, p. 636 - 637
  • 20
  • [ 393-52-2 ]
  • [ 1711-06-4 ]
  • [ 80277-41-4 ]
  • [ 5955-74-8 ]
Reference: [1] Patent: US6359156, 2002, B1, . Location in patent: Page column 10
  • 21
  • [ 393-52-2 ]
  • [ 445-28-3 ]
Reference: [1] Chemische Berichte, 1937, vol. 70, p. 1416,1419
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2544 - 2546
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3263 - 3270
  • 22
  • [ 393-52-2 ]
  • [ 399-31-5 ]
Reference: [1] Chemische Berichte, 1937, vol. 70, p. 1416,1419
  • 23
  • [ 6148-64-7 ]
  • [ 393-52-2 ]
  • [ 1479-24-9 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With triethylamine; magnesium chloride In acetonitrile at 20℃; for 0.5 h;
Stage #2: With triethylamine In acetonitrile at 20℃;
Experimental operation: Take malonate potassium salt 1.00 g (about 5.47mmol) of anhydrous magnesium chloride and 0.65 g (About 6.84mmol) in 25 mLround bottom flask was added dropwise 0.55 g of triethylamine was added after 6mL of acetonitrile was dissolved, stirred 30 min at room temperature. Thendropped by 2 mL of acetonitrile was dissolved 0.48 g (2.5 mmol) o-fluorobenzoyl chloride ld, supplemented triethylamine 0.06 mL, stirred atroom temperature overnight. After treatment: 30 mL of water was added to dilutethe reaction solution, and then were added 30,20,20 mL ethyl acetate, and theethyl acetate layer was collected. After 30 mL with saturated brine ethylacetate layer was dried over anhydrous sodium sulfate, and spin dry columnchromatography (PE: EA = 15: 1) to give the product isolated 2d, in 92percent yield.
13.5 g
Stage #1: With triethylamine; magnesium chloride In tetrahydrofuran at 10 - 35℃; for 8.5 h;
Stage #2: at 15 - 35℃; for 16 h;
Example-12: Preparation of compound of Formula Xlla. 2-fluorobenzoic acid (lOg) toluene (80ml) and dimethyl formamide (0.1ml) were charged into a round bottom flask at 25-35°C. To the reaction mass thionyl chloride (12.7g) was added slowly over a period of 30min at same temperature. Reaction mass was heated to reflux and stirred for 3-4hr. After completion of the reaction, reaction mass was cooled to 55-65°C and distilled completely under vacuum at 55-65°C and co-distilled with toluene (2x20ml) to obtain residue and the residue was dissolved in tetrahydrofuran (50ml). Tetrahydrofuran (150ml) and magnesium chloride (24.5g) was added in another round bottom flask at 25-35°C. Reaction mass was cooled to 10-15°C and was added potassium salt of monoethylmalonate (36.4g) at same temperature. To the reaction mass was added triethyl amine (21.6g) slowly over a period of 30min and reaction mass was heated to 25- 35 °C and stirred for 8hr at same temperature. To the reaction mass was added above pre dissolved tetrahydrofuran solution of 2-fluorobenzoyl chloride at 15-25°C and stirred for 16hr at 25-35°C. After completion of the reaction, reaction mass was distilled completely under vacuum at below 50°C and cooled to 25-35°C. To the resultant reaction mass was added water (400ml) and stirred for 3hr at same temperature. Filtered the precipitated solids and washed with water (10ml). The obtained solids were stirred with water (200ml), and a mixture of water (100ml) and sodium bicarbonate (50g), a mixture of water (100ml) and hydrochloric acid (10ml) sequentially at 25-35°C and filtered the solid and washed with water (10ml). The obtained solid was stirred with methanol (20ml) for 40min at 25-35°C. Filtered the solids and washed with methanol (10ml) and dryed the material to obtain title compound. Yield: 13.5 g.
Reference: [1] Patent: CN105663112, 2016, A, . Location in patent: Page/Page column 15
[2] Patent: WO2017/37672, 2017, A1, . Location in patent: Page/Page column 49; 50
  • 24
  • [ 1071-46-1 ]
  • [ 393-52-2 ]
  • [ 1479-24-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 3, p. 620 - 625
  • 25
  • [ 393-52-2 ]
  • [ 1479-24-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2843 - 2855
[2] Archiv der Pharmazie, 2013, vol. 346, # 7, p. 521 - 533
[3] Patent: EP2799437, 2014, A1,
[4] Patent: US2014/364431, 2014, A1,
  • 26
  • [ 35227-78-2 ]
  • [ 393-52-2 ]
  • [ 1479-24-9 ]
Reference: [1] Synthesis, 1983, # 1, p. 52 - 53
  • 27
  • [ 352-13-6 ]
  • [ 393-52-2 ]
  • [ 342-25-6 ]
YieldReaction ConditionsOperation in experiment
72% at 25℃; for 1 h; General procedure: 2-Fluorobenzoyl chloride (6 mmol, 1.0 eq) in 2-methyltetrahydrofuran (15 mL) and Compound 2 (9 mmol,1.5 eq) of 2-methyltetrahydrofuran solution (15 mL) passed through material channels A and B, respectively, via metering pumps P1, P2.Mixing into a mixing module M having a preset temperature of 25 ° C at a flow rate of 1 mL/min,After staying in the reaction module L for 1 h,The reaction solution flows out from the outlet D.The reaction liquid flowing out from the outlet D was collected in a 1 mol/L hydrochloric acid solution.Quenched by stirring,Saturated saline solution,Dry over anhydrous sodium sulfate,Post-treatment by concentration, column chromatography, etc.Compound 5 was obtained.
Reference: [1] Patent: CN108409516, 2018, A, . Location in patent: Paragraph 0049-0052
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 662
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  • [ 342-25-6 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 4, p. 446 - 447
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 662
[3] Russian Chemical Bulletin, 2001, vol. 50, # 7, p. 1208 - 1213
  • 29
  • [ 74-85-1 ]
  • [ 393-52-2 ]
  • [ 651735-59-0 ]
YieldReaction ConditionsOperation in experiment
2.5 g With aluminum (III) chloride; sodium chloride In dichloromethane for 2 h; Cooling with ice As presented in the following reaction formula, a crude product of Compound 2 was dissolved in methylene chloride (50 mL). Under cooling with ice, aluminum chloride (AlCl3; 13 g, 9.7 mmol) and sodium chloride (NaCl; 6 g, 10 mmol) were added to the resulting solution, and ethylene gas was introduced for 2 hours to the mixture under stirring. Then, 100 g of ice was added to the reaction mixture, followed by filtrating. The filtrate was extracted three times with 30 mL of ether and then washed with 100 mL of saturated brine. The filtrate was dried and concentrated with anhydrous sodium sulfate, and purified with a silica gel column of 100 g using n-hexane and ethyl acetate, to thereby give Compound 3 of interest (2.5 g, yield: 23percent).
2.5 g With aluminum (III) chloride; sodium chloride In dichloromethane for 2 h; Cooling with ice As presented in the following reaction formula, a crude product of Compound 2 was dissolved in methylene chloride (50 mL). Under cooling with ice, aluminum chloride (AlCl3; 13 g, 9.7 mmol) and sodium chloride (NaCl; 6 g, 10 mmol) were added to the resulting solution, and ethylene gas was introduced for 2 hours to the mixture under stirring. Then, 100 g of ice was added to the reaction mixture, followed by filtrating. The filtrate was extracted three times with 30 mL of ether and then washed with 100 mL of saturated brine. The filtrate was dried and concentrated with anhydrous sodium sulfate, and purified with a silica gel column of 100 g using n-hexane and ethyl acetate, to thereby give Compound 3 of interest (2.5 g, yield: 23percent).
Reference: [1] Patent: EP2647622, 2013, A1, . Location in patent: Paragraph 0125
[2] Patent: US2013/317110, 2013, A1, . Location in patent: Paragraph 0140
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  • [ 393-52-2 ]
  • [ 651735-59-0 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10195 - 10198
  • 31
  • [ 393-52-2 ]
  • [ 775304-57-9 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With hydroxylamine In water; <i>tert</i>-butyl alcohol at 38 - 41℃; for 21 h;
Stage #2: With triethylamine In water; <i>tert</i>-butyl alcohol at 27 - 40℃; for 7 h;
3-[5-(2-fluorophenylHl,2,41oxad-azol-3-vπ-benzoic acid: One pot process; Reflux <n="25"/>[0188] A reactor vessel was charged with 3-Cyanobenzoic acid (7.35 g) and molten ter/-butanol (100 raL). The vessel was sealed and the batch temperature was set to 600C and the agitator was started. The suspension was stirred for Ih and then the batch temperature was set to 400C. 50percent aqueous hydroxylamine (3.63 g) was charged to the reactor in an inert atmosphere over 3 hours. The batch temperature was maintained at 38- 410C during the addition. The reaction was completed after stirring for 18 hours at 400C. [0189] The batch was cooled to 27°C and charged with triethylamine (5.56 g) over 2 minutes. 2-Fluorobenzoyl chloride (7.82 g) was added over 3 hours. The batch temperature was maintained at 24-27°C during the addition. The batch was stirred for further 4 hours at 400C.[0190] The batch was heated to 790C over 30 minutes and stirred for 16 hours at about 79°C. To the white suspension was added water (100 mL) over 3 hours while the batch temperature was maintained at 700C. The batch was charged with 37percent aqueous hydrochloric acid over 20 minutes. The pH of the batch was determined to be about 2.2, by a pH meter and stirring at about 700C was continued for about an additional 1 hour. [0191] The batch was cooled in a linear fashion from 700C to 300C over 3 hours and the slurry was transferred into a filter. Filtration was complete after 5 minutes. The filter cakes were washed with fer/-butanol (50 mL, 40 0C) over 5 minutes. Purified water (100 mL, 600C) was applied to the cakes as the final wash. The cakes were dried in a vacuum oven at 70 0C for 18 hour and then discharged. Purity was determined to be about 98.68percent. The overall yield of isolated product was about 76percent (10.8 g).
Reference: [1] Patent: WO2008/30570, 2008, A1, . Location in patent: Page/Page column 23-24
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  • [ 1141475-82-2 ]
  • [ 393-52-2 ]
  • [ 775304-57-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 11, p. 2473 - 2476
  • 33
  • [ 1141475-82-2 ]
  • [ 393-52-2 ]
  • [ 775304-60-4 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In acetone at 20℃; for 24 h; General procedure: 2 mmol of either amidoxime 1 [30] or 2 [26] were dissolved in acetone (200 mL) in a round-bottomed flask; then, K2CO3 (0.35 g; 2.5 mmol) and the corresponding aroyl chloride (2.5 mmol), were added to the reaction mixture and stirred for 24 h at room temperature. The solvent was removed under vacuum and the residue treated with water and refluxed for 30 min 1,2,4-Oxadiazoles products were obtained by filtration and further purified by chromatography.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 236 - 244
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 11, p. 2473 - 2476
  • 34
  • [ 6638-79-5 ]
  • [ 393-52-2 ]
  • [ 198967-24-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.166667 h;
Stage #2: at 0 - 20℃;
Triethylamine (5.32 mL, 37.84 mmol) was added dropwise to a solution of Ν,Ο-dimethylhydroxylamine hydrochloride (2.768 g, 28.38 mmol) in anhydrous dichloromethane (45 mL) at 0 °C. After stirring for 10 min, 2-fluorobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise. The reaction mixture was returned to room temperature and stirred for 5 h. The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2 x 60 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.1 16, 17 mmol) in a 90percent yield. [0
90%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.166667 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 5 h; Inert atmosphere
Triethylamine (5.32 mL, 37.8 mmol) was added dropwise to a solution of N,O-dimethylhydroxylamine hydrochloride (2.77 g, 28.4 mmol) in anhydrous dichloromethane (45 mL) at 0 °C.
After stirring for 10 min, 2-flurobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise.
The reaction mixture was returned to room temperature and stirred for 5 h.
The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2 * 60 mL).
The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure.
Purification using flash chromatography (silica gel, hexanes/ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.12 g, 17.0 mmol, 90percent yield).
1H NMR (500 MHz, CDCl3): δ 7.44-7.38 (2H, m), 7.19 (1H, t, J = 7.5 Hz), 7.10 (1H, t, J = 8.9 Hz), 3.55 (3H, br s), 3.35 (3H, br s).
13C NMR (125 MHz, CDCl3): δ 166.40, 158.66, (d, J = 249 Hz), 131.50, 128.90, 124.11, 123.52 (d, J = 17 Hz), 115.69 (d, J = 21 Hz), 61.21, 32.31. 19F NMR (470 MHz, CDCl3): δ -114.04 (1F, s). HRMS (ESI) calculated for C9H10FNO2H+ (M+H)+ 184.07683, found 184.07702.
62% With pyridine In tetrahydrofuran at 0 - 20℃; for 2.25 h; N,O-Dimethylhydroxylamine hydrochloride (23.4 g, 240 mmol) was suspended inTHF (100 ml) and cooled to 0 °C under nitrogen. Pyridine (32 ml, 400 mmol) was addedslowly. A solution of 2-fluorobenzoyl chloride (9.5 ml, 80 mmol) in THF (50 ml) was addedover 15 min. The reaction was removed from the ice bath and stirred at rt for 2 h. Water (100ml) and AcOEt (100 ml) were added, and the phases were separated. The aq. phase wasextracted with AcOEt (100 ml). The organic phases were pooled and washed with 1 N HCI (2x 100 ml) and 1 N NaOH (100 ml). After drying over MgSO4, the sample was concentrated toyield a yellow oil (10.7 g). The oil was purified by vacuum distillation, and a colorless oil wascollected (0.22 torr, 57-59 °C, 9.1 g, 62percent yield)2-fluoro-N-methoxy-N-methylbenzamide1H-NMR (300MHz, CDCI3) 53.34 (s, 3H), 3.54 (br, 3H), 7.10 (m, 1H), 7.19 (m, 1H),7.42 (m, 2H)
Reference: [1] RSC Advances, 2013, vol. 3, # 26, p. 10158 - 10162
[2] Patent: WO2013/142038, 2013, A2, . Location in patent: Paragraph 0130
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6974 - 6992
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1415 - 1419
[5] Patent: WO2006/3096, 2006, A1, . Location in patent: Page/Page column 73
[6] Chemical Communications, 2012, vol. 48, # 71, p. 8976 - 8978
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  • [ 393-52-2 ]
  • [ 1117-97-1 ]
  • [ 198967-24-7 ]
YieldReaction ConditionsOperation in experiment
84.6% With triethylamine In dichloromethane at 0 - 20℃; To a solution of 2-fluorobenzoyl chloride (50 g, 0.31 mol) in CH2Cl2 (200 mL) was added N,O-dimethylhydroxylamine (46 g, 0.47 mol), and a solution of triethylamine (127 g, 1.26 mol) in CH2Cl2 (100 mL) at 0° C. The reaction mixture was warmed slowly to rt, and stirred for 3 h. The mixture was quenched with iced water and extracted with CH2Cl2 (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford 2-fluoro-N-methoxy-N-methylbenzamide (48 g, yield: 84.6percent).
Reference: [1] Patent: US2010/331320, 2010, A1, . Location in patent: Page/Page column 51; 52
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