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Product Citations

Hegde, Pooja ; Orimoloye, Moyosore O. ; Sharma, Sachin , et al. DOI: PubMed ID:

Abstract: Tuberculosis (TB), caused by Mycobacterium tuberculosis (Mtb) is a leading cause of infectious disease mortality. The salicylic acid derived small mol. siderophores known as mycobactins are essential in vivo for iron acquisition of Mtb where iron is restricted in the host. Herein, we synthesize and explore the mechanism of action of polyfluorinated salicylic acid derivates, which were previously reported to possess potent antimycobacterial activity. We hypothesized fluorinated salicylic acid derivates may inhibit mycobactin biosynthesis through initial bioactivation and conversion to downstream metabolites that block late steps in assembly of the mycobactins. Enzymic studies demonstrated that some of the fluorinated salicylic acid derivatives compounds were readily activated by the bifunctional adenylating enzyme MbtA, responsible for incorporation of salicylic acid into the mycobactin biosynthetic pathway; however, they did not inhibit mycobactin biosynthesis as confirmed by LS-MS/MS using an authentic synthetic mycobactin standard Further mechanistic anal. of the most active derivative (Sal-4) using an MbtA-overexpressing Mtb strain as well as complementation studies with iron and salicylic acid revealed Sal-4 cannot be antagonized by overexpression of MbtA or through supplementation with iron or salicylic acid. Taken together, our results indicate the observed antimycobacterial activity of polyfluorinated salicylic acid derivative is independent of mycobactin biosynthesis.

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Product Details of [ 69-72-7 ]

CAS No. :69-72-7 MDL No. :MFCD00002439
Formula : C7H6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :YGSDEFSMJLZEOE-UHFFFAOYSA-N
M.W : 138.12 Pubchem ID :338
Synonyms :
2-Hydroxybenzoic acid;NSC 180
Chemical Name :2-Hydroxybenzoic acid

Calculated chemistry of [ 69-72-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.42
TPSA : 57.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 2.26
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 0.99
Log Po/w (SILICOS-IT) : 0.74
Consensus Log Po/w : 1.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.439 mg/ml ; 0.00318 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.109 mg/ml ; 0.000786 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.17
Solubility : 9.4 mg/ml ; 0.0681 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 69-72-7 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P201-P202-P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P308+P313-P405-P501 UN#:N/A
Hazard Statements:H302-H318-H361 Packing Group:N/A
GHS Pictogram:

Applications of [ 69-72-7 ]

Salicylic acid (CAS: 69-72-7) can be used in the preparation of Sulfasalazine (Azulfidine) (CAS: 599-79-1). Sulfasalazine is indicated for managing inflammatory diseases such as ulcerative colitis and rheumatoid arthritis (RA).

Application In Synthesis of [ 69-72-7 ]

* 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 [ 69-72-7 ]
  • Downstream synthetic route of [ 69-72-7 ]

[ 69-72-7 ] Synthesis Path-Upstream   1~72

  • 1
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 10, p. 3020 - 3028
  • 2
  • [ 76809-21-7 ]
  • [ 1824-81-3 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 10, p. 3020 - 3028
  • 3
  • [ 76809-23-9 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 10, p. 3020 - 3028
  • 4
  • [ 76809-27-3 ]
  • [ 3430-27-1 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 10, p. 3020 - 3028
  • 5
  • [ 76809-24-0 ]
  • [ 3430-10-2 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 10, p. 3020 - 3028
  • 6
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  • [ 56341-31-2 ]
Reference: [1] Journal of the Chemical Society, 1920, vol. 117, p. 1063
  • 7
  • [ 65-45-2 ]
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  • [ 1218-69-5 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene at 10 - 40℃; for 1.5 h;
Stage #2: at 25 - 120℃; for 2 h;
Xvlene (150 mL) and salicylic acid (1) (100 g, 0,072 mol) were added to a 500 mL, 4 necked round-bottom flask equipped with a mechanical stirrer and thermocouple. Thion I chloride (87 g, 0.036 mol)) was added at 10°C to 15°C. After addition of thionyl chloride, the reaction mass was stiired at 10°C to 15°C for 30 minutes, The reaction mass was further heated at 35°C-40°C for 1 hr. A solution of salicylamide (2) (100 g, 0.072 mol) in 200 mL of xylene was added to the reaction mass at 25°C to 30°C. After addition, the reaction mass was gradually heated at 80°C to 120°C and stirred for 2 hrs, After completion of reaction, excess of xvlene was removed under vaccum. Methanol 200 mL was added to the reaction mass at 70°C to 80°C and stirred for 1 hour. The reaction mass was cooled gradually at 25°C to 30°C. The solid was filtered and washed with methanol and dried at 55°C to 60°C under vacuum tray drier to yield 165 g 2-(2-hvdroxyphenvI)-4- 1 ,3-benzoxazin-4-one (3). Yield 95percent, rn.p. 239°C. LCMS: m/z = 240.22 (M+H) calcd, for C14H9N30: 239.2.
76% With pyridine; thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene at 20℃; Reflux Salicylic acid (6.04 g, 43.75 mmol), salicylamide (5.00 g, 36.46 mmol) and pyridine (0.37 mL, 4.63 mmol) were heated at reflux in xylene (18.00 mL) for 15 min.
Thionyl chloride (5.83 mL, 80.21 mmol) was added with vigorous stirring over a period of 4 h, with further stirring for 16 h at room temperature.
Xylene was removed by concentration in vacuo, and resulting solid residue was suspended in ethanol (15.00 mL) and acetic acid (0.36 mL).
The mixture was heated to reflux and cooled to room temperature.
The solid precipitate was isolated and dried to yield 2-(2-Hydroxyphenyl)-benzo-4H-[1,3]-oxazin-4-one (1) (6.59 g, 27.54 mmol, 76percent) as yellow solid.
54% With 1,3,5-trichloro-2,4,6-triazine; triethylamine In toluene at 80℃; for 16 h; Dean-Stark; Inert atmosphere In a round bottom flask fitted a reflux condenser and a Dean-Stark trap, a suspension of salicylic acid (27.6 g, 0.2 mol), salicylamide (23.3 g, 0.17 mol) and 2,4,6-trichloro-1,3,5-triazine (24.8 g, 0.134 mol) in 600 mL toluene was heated under a nitrogen atmosphere for 30 minutes at 80C. Then triethylamine (28.08 mL, 0.2 mol) was added slowly to the solution and the resulting mixture was heat to reflux for 16 h. Precipitation of some solid began to occur during the reaction; the reaction mixture was cooled to about 80C and then filtered hot (by suction) as quickly as possible to remove the solid mixture of triethylamine hydrochloride, cyanuric acid and other solids. The filtrate was then evaporated and the resulting crude solid was recrystallized39 from ethanol (600 mL) to give21.9 g (54percent yield) of benzoxazinone 4 in better than 98percent purity as a very pale yellow solid. All spectroscopic data of product 4 matched those of an authentic sample.
39.3%
Stage #1: With N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride In dichloromethane; water at 0 - 30℃; for 2.41667 h;
Stage #2: at 85 - 160℃; for 3 h;
Example 1
Preparation of 2-(2-hydroxyphe41)-benz[1,3]oxazin-4-one
A mixture of dichloromethane (200 ml), salicylic acid (50.0 gm) and p-toulenesulfonyl chloride (69 gm) were cooled to 10-15° C. Diisopropyl ethyl-amine (139.0 ml) was added drop-wise to the above mixture at 10-20° C.
Reaction mass was stirred for 10 min at 10-20° C. and raised the temperature to 25-30° C.
The reaction was maintained for 2 hours at 25-30° C.
Reaction mass was cooled 0-5° C. Purified water (200 ml) was charged to the above mixture and stirred for 15 minutes.
The layers were separated.
Salicylamide (39.6 gm) and toluene (200.0ml) were heated to 85-90° C. and the above organic layer was added drop-wise into salicyliamide solution with simultaneous distillation of solvent at 85-90° C. and distilled the solvent upto the reaction mass temperature reaches to 110-120° C. and further reaction was maintained for 3hrs at 110-120° C.
Further solvent was distilled under atmospheric pressure upto reaction mass temperature reaches to 140-160° c and further the reaction was maintained for 1-2 hrs at 140-160° C. until the starting material disappears.
Reaction mass was cooled to 75-80° C. and distilled off completely toluene under vacuum.
Ethanol (50 ml) was added to the above reaction mass at 75-80° C.
Reaction was stirred for 15 min and distilled off the ethanol at 75-80° C. Further ethanol (50.0 ml) was added stir for 5-10 min.
Ethanol was distilled off completely under vacuum at 75-80° C. Ethanol (150 ml) was charged into above contents at 75-80° C.
The contents were maintained for 1 hour at 75-80° C. and slowly cooled to 0-5° C.
Reaction mass was maintained for 2 hrs at 0-5° C.
The reaction mass was filtered and washed with ethanol (50.0 ml).
Dried the compound at 50-55° C. Yield: 39.30percent.
39% With pyridine; thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene; ethanol for 4 h; Reflux Salicylic acid (2 g, 14.5 mmol), salicylamide (1.53 g, 11.1 mmol)and pyridine (1 ml) were refluxed in xylene (20 mL). Thionylchloride (1.9 g, 16.0 mmol) was added with vigorous stirring over aperiod of 4 h. An intense evolution of SO2 and HCl was noted. At theend of the reaction, the product started to crystallize. Stirring wascontinued for an additional 30 min, and the xylenewas removed byreduced-pressure distillation. The resulting solid residue was suspendedin EtOH (30 mL) and acetic acid (1 mL). The mixture washeated gently and then allowed to cool to 20 C. The precipitatewasfiltered and recrystallized from 2-methoxyethanol (35 mL). Yield:yellow-green solid (1.04 g, 4.34 mmol, 39percent). m.p. 202.2e204.6 C.1H NMR (500 MHz, DMSO-d6) d12.95 (s, 1H), 8.25e8.21 (m, 1H),8.08 (dd, J1 7.8, J2 1.5 Hz, 1H), 7.98e7.94 (m, 1H), 7.81 (dd,J1 8.4, J2 0.6 Hz, 1H), 7.68e7.60 (m, 2H), 7.13e7.08 (m, 2H). ESIMS:m/z. Calculated for C14H9NO3 239.06; found[MH] 240.0655.

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[13] Synthetic Communications, 2012, vol. 42, # 21, p. 3200 - 3210
[14] Patent: US2014/39199, 2014, A1, . Location in patent: Paragraph 0043
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[2] Patent: EP2460799, 2012, A1,
[3] Patent: WO2012/131017, 2012, A1,
  • 9
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Reference: [1] Chemicke Listy, 1938, vol. 32, p. 292[2] Chem. Zentralbl., 1939, vol. 110, # I, p. 795
[3] Justus Liebigs Annalen der Chemie, 1857, vol. 103, p. 45,50
[4] Justus Liebigs Annalen der Chemie, 1875, vol. 179, p. 107
[5] Chemische Berichte, 1900, vol. 33, p. 3238
[6] Gazzetta Chimica Italiana, 1888, vol. 18, p. 346,351
  • 10
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  • [ 97-05-2 ]
Reference: [1] Gazzetta Chimica Italiana, 1888, vol. 18, p. 346,351
  • 11
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Reference: [1] Justus Liebigs Annalen der Chemie, 1875, vol. 179, p. 107
[2] Chemische Berichte, 1900, vol. 33, p. 3238
  • 12
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Reference: [1] Justus Liebigs Annalen der Chemie, 1857, vol. 103, p. 45,50
  • 13
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  • [ 21725-69-9 ]
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5301 - 5303
  • 14
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  • [ 35748-34-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 4081 - 4085
[2] Patent: CN104788398, 2017, B,
  • 15
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  • [ 89-73-6 ]
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5301 - 5303
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1624 - 1626
  • 16
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  • [ 13099-95-1 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 21, p. 5584 - 5587
  • 17
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  • [ 5381-99-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5602 - 5604
[2] Patent: WO2005/63781, 2005, A1, . Location in patent: Page/Page column 31
[3] Patent: WO2005/63781, 2005, A1, . Location in patent: Page/Page column 31
[4] Russian Journal of Organic Chemistry, 2018, vol. 54, # 9, p. 1333 - 1336[5] Zh. Org. Khim., 2018, vol. 54, # 9, p. 1321 - 1324,4
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  • [ 6083-10-9 ]
  • [ 80337-06-0 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 6015 - 6017
  • 19
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  • [ 7719-12-2 ]
  • [ 5381-99-7 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1672
[2] Chemistry and Industry (London, United Kingdom), 1954, p. 402
  • 20
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  • [ 50-78-2 ]
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Reference: [1] Archiv der Pharmazie, 1985, vol. 318, # 2, p. 120 - 127
  • 22
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  • [ 1761-62-2 ]
Reference: [1] Patent: WO2008/57336, 2008, A2, . Location in patent: Page/Page column 80
  • 23
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  • [ 2136-89-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1887, vol. 239, p. 321
[2] Justus Liebigs Annalen der Chemie, 1860, vol. 115, p. 194
[3] Justus Liebigs Annalen der Chemie, 1927, vol. 454, p. 78,103
  • 24
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  • [ 80-09-1 ]
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  • 25
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  • [ 91983-31-2 ]
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  • 26
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  • [ 1666-28-0 ]
YieldReaction ConditionsOperation in experiment
100% With sulfuric acid; C20H22Br2N2O5V; dihydrogen peroxide In methanol; water at 20℃; for 0.416667 h; General procedure: In a 10-mL round-bottom flask equipped with a magnetic stirring bar, 1 mM of the 2-nitrophenol was reacted with different amounts of the oxidant, acid, bromide source, and the vanadyl Schiff base complex in 4 mL of solvent. The content was stirred at room temperature.The progress of the reaction was monitored by GLC.
Reference: [1] Journal of Coordination Chemistry, 2014, vol. 67, # 22, p. 3664 - 3677
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  • [ 4431-00-9 ]
Reference: [1] Patent: US2013/35388, 2013, A1, . Location in patent: Paragraph 0040
[2] Patent: WO2014/9779, 2014, A1, . Location in patent: Paragraph 3
  • 28
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Reference: [1] Chemische Berichte, 1892, vol. 25, p. 947
[2] Analytical Chemistry, 1949, vol. 21, p. 1334,1337
[3] Journal of the American Chemical Society, 1940, vol. 62, p. 989
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Reference: [1] Journal of Research of the National Bureau of Standards (United States), 1938, vol. 21, p. 113
[2] Chim. farm. Promysl., 1933, p. 271[3] Chem. Zentralbl., 1934, vol. 105, # II, p. 2216
[4] Organic Syntheses, 1929, vol. 9, p. 8[5] Organic Syntheses, 1947, vol. Coll. Vol. I, p. 54
[6] Bur. Stand. J. Res., 1938, vol. 21, p. 113
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  • 34
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  • [ 14714-50-2 ]
Reference: [1] Tetrahedron, 2015, vol. 71, # 26-27, p. 4432 - 4437
  • 35
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  • [ 87-20-7 ]
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  • [ 610-04-8 ]
  • [ 616-76-2 ]
YieldReaction ConditionsOperation in experiment
55.7%
Stage #1: With copper(I) oxide In trifluoroacetic acid for 5 h; Reflux
Stage #2: With hydrogenchloride In water at 20℃; for 1 h;
General procedure: To a solution of substrates (1a–1q, 0.15 mmol) in trifluoroacetic acid (5 ml), hexamethylenetetramine (0.3 mmol) and cuprous oxide (0.15 mmol) were added. The reaction mixture was refluxed for about 5 h, cooled to room temperature, followed by addition of hydrochloric acid (3 N, 5 ml). After stirring for another 1 h, the solution was concentrated under reduced pressure. The products were purified by silica gel column chromatography (200–300 mesh).
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YieldReaction ConditionsOperation in experiment
2.2 g at 100℃; for 16 h; To a solution of 2-hydroxybenzoic acid (2.0 g, 14.5 mmol) in water, hexamethylen5 etetramine (4.05 g, 28.9 mmol) was added and refluxed at 10000 for 16 h. Aftercooling, the reaction mixture was acidified with 1 N HCI (pH=3) and extracted with ethyl acetate, washed with water and dried. The product was obtained by concentrating under vacuo to yield the title compound (2.2 g,) as a yellow solid.LCMS: (M-H) = 165.1
2.2 g at 100℃; for 16 h; To a solution of 2-hydroxybenzoic acid (2.0 g, 14.5 mmol) in water hexamethylenetetramine (4.05 g, 28.9 mmol) was added and refluxed at 100°C for16 h. After cooling, the reaction mixture was acidified with iN HCI (PH=3) and extracted with ethyl acetate, washed with water and dried. The product was obtained by concentrating under vacuo to yield the title compound (2.2 g,) as a yellow solid.LOMS: (M-H) = 165.1
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  • 38
  • [ 50-00-0 ]
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  • [ 616-76-2 ]
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[2] Patent: DE105798, , ,
  • 39
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[2] Journal of the Chemical Society, 1936, p. 554
  • 40
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  • [ 610-04-8 ]
  • [ 616-76-2 ]
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  • [ 64-19-7 ]
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  • [ 610-04-8 ]
  • [ 616-76-2 ]
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YieldReaction ConditionsOperation in experiment
95.4%
Stage #1: With hydrogenchloride; sodium nitrite In water at 2℃; for 0.333333 h;
Stage #2: With sodium hydroxide In water at 7℃; for 1.5 h;
Example 4
Place sulfapyridine and 4 (amount of substance) hydrochloric acid (amount of substance of sulfapyridine is for 1) in a reaction flask. Stir until dissolve. Adjust temperature to 2°C then start dropping 1.10sodium nitrite ( amount of substance of sulfapyridine is 1m).Allocate aqueous solution. React for 20min to obtain a solution containingdiazonium salt intermediate. Name this to be A. Place 1.3 salicylic acid and part of sodium hydroxide ( amount ofsubstance of sulfapyridine is 1m ) in a reaction flask. After adjustingtemperature to 7°C,slowly start dropping the above-mentioned A to the above-mentioned reactionflask. At the same time, drop the remaining sodium hydroxide solution to controlthe pH of the reaction liquid to 10. Start reaction. The used amount of sodiumhydroxide is 4 (amount ofsubstance of sulfapyridine is 1m ). React for 1.5h. Stop reaction. Add THF tothe reaction mixture. Add hydrochloric acid to adjust pH to 3. Heat underreflux for a period of time. Cool to 30°C to crystallize. Filter out crystals to obtain crudesulfasalazine. Place 10g crude sulfasalazine,70g dimethyl sulfoxide, 30g water in 250mL flask. Also, add solid sodiumhydroxide to mixture with pH of 9. Heat the mixture in the flask to 80oCto fully dissolve. After dissolving, add hydrochloric acid, dropwise, to adjustthe pH of the solution to 1. Incubate at 80°Cfor 2h then cool to 0°C then filter to obtain crude crystals. Add crystalsto water. Add solid sodium hydroxide. Heat to 80°C. Dissolve to obtain solutionwith pH 9. Sequentially, undergo, at 70°C, decolorization using 7g activatedcharcoal and filtration. Add, dropwise, hydrochloric acid to crystals with pH1.Dry crystals to obtain pure sulfasalazine. In this case, 9.54g ofpure sulfasalazineare collected. Yield is 95.4percent. HLPC purity test shows 99.7percent.
Reference: [1] Patent: CN105348184, 2016, A, . Location in patent: Paragraph 0049; 0050; 0051; 0052; 0053
[2] Patent: CN105330599, 2016, A, . Location in patent: Paragraph 0045; 0046
[3] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 1987 - 2004
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YieldReaction ConditionsOperation in experiment
94.9% at 7℃; for 1.5 h; into the reaction bottle placed Salicylic acid and partialsodium hydroxide with a material amount of 1.3(with the material amount ofSulfapyridine is 1). After the temperature was controlled to 7 ° C, A wasgradually dropped into the above reaction bottle and simultaneously theremaining sodium hydroxide solution was dropped to control the pH of thereaction solution to 10 to initiate the reaction. The amount of sodiumhydroxide used is 4 (based on the material amount of Sulfapyridine is 1).after1.5h of reaction the reaction was stopped. In to the reaction mixture acetonewas added then the pH was adjusted to 3 with the addition of acid, and thetemperature was refluxed for a period of time. And then cooled to 30 ° C toprecipitate crystals. The crystals were filtered off and the crystals werewashed several times to obtain sulfasalazine. The yield of this example was 94.9percent,and the purity was 98.6percent by HPLC.
Reference: [1] Patent: CN105367489, 2016, A, . Location in patent: Paragraph 0032; 0033
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Reference: [1] Patent: WO2011/21218, 2011, A2,
[2] Patent: US2011/97413, 2011, A1,
[3] Patent: WO2012/25935, 2012, A2,
[4] Patent: WO2012/131017, 2012, A1,
[5] Synthetic Communications, 2012, vol. 42, # 21, p. 3200 - 3210
[6] Patent: WO2011/70560, 2011, A1,
[7] Patent: US2016/24025, 2016, A1,
[8] Patent: US2016/24025, 2016, A1,
[9] Patent: US2016/296629, 2016, A1,
[10] Patent: CN108727287, 2018, A,
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