Home Cart 0 Sign in  
X

[ CAS No. 1711-06-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 1711-06-4
Chemical Structure| 1711-06-4
Chemical Structure| 1711-06-4
Structure of 1711-06-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1711-06-4 ]

Related Doc. of [ 1711-06-4 ]

Alternatived Products of [ 1711-06-4 ]

Product Details of [ 1711-06-4 ]

CAS No. :1711-06-4 MDL No. :MFCD00000681
Formula : C8H7ClO Boiling Point : -
Linear Structure Formula :- InChI Key :YHOYYHYBFSYOSQ-UHFFFAOYSA-N
M.W : 154.59 Pubchem ID :74375
Synonyms :

Calculated chemistry of [ 1711-06-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.59
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) : -4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 3.35
Log Po/w (WLOGP) : 2.37
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 2.8
Consensus Log Po/w : 2.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.29
Solubility : 0.0798 mg/ml ; 0.000516 mol/l
Class : Soluble
Log S (Ali) : -3.39
Solubility : 0.0636 mg/ml ; 0.000411 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.33
Solubility : 0.0718 mg/ml ; 0.000465 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.1

Safety of [ 1711-06-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1711-06-4 ]

* 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 [ 1711-06-4 ]
  • Downstream synthetic route of [ 1711-06-4 ]

[ 1711-06-4 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 1711-06-4 ]
  • [ 1129-28-8 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 1180,1181
[2] Organic and biomolecular chemistry, 2004, vol. 2, # 12, p. 1732 - 1741
[3] Farmaco, Edizione Scientifica, 1987, vol. 42, # 6, p. 409 - 424
[4] RSC Advances, 2013, vol. 3, # 45, p. 23119 - 23127
  • 2
  • [ 67-56-1 ]
  • [ 1711-06-4 ]
  • [ 1129-28-8 ]
Reference: [1] Chem.Abstr., 1964, vol. 60, # 15802,
[2] Chem.Abstr., 1965, vol. 62, # 14577,
[3] Chem.Abstr., 1966, vol. 65, # 5406,
  • 3
  • [ 99-04-7 ]
  • [ 1711-06-4 ]
YieldReaction ConditionsOperation in experiment
99.3% at 90℃; for 3 h; In a 1000 ml reaction flask equipped with a thermometer, a stirrer, a condenser, and an exhaust gas absorption device, 540.56 g of m-toluic acid, 573.0 g of thionyl chloride and 1.0 g of N, N-dimethylformamide were charged and heated to 90 ° C, the reaction was stirred 3h, the reaction was completely transparent, excess pressure to remove excess thionyl chloride, m-methyl benzoyl chloride 610.0g, purity 98.2percent, yield 99.3percent o
98.2% With thionyl chloride; tetra(n-butyl)ammonium hydrogensulfate In 5,5-dimethyl-1,3-cyclohexadiene at 45℃; for 4.5 h; Large scale m-methyl benzoyl chloride continuous production process is as follows: (1) m-methylbenzoic acid 1360kg, 1453kg thionylchloride and 2720kg xylene were added to the reactor. Then, addition of 2.04kg tetrabutyl ammonium hydrogen sulfate. At 45 deg.C reaction 4h, until no gas evolution. Continue to hold temperature for 0.5 hours, to obtain a reaction solution;(2) The reaction mixture was added tothe distillation column, flow into the tower 4.7kg / min, distillation tower bottoms heated by steam, Temperature controlled at 105 , overhead light component recovery flow 4.2kg / min, light component after condensed by the condenser returned to the reaction vessel; (3) the distillation tower reactor m-methylbenzoyl chloride crude product was added to the thin film evaporator, feed rate of 3.9kg / min, adjust the degree of vacuum to 630mmHg, vacuum distillation at 127 deg.C, to give 1516.5 kg-methyl chloride in a yield of 98.2percent, after testing, chromatography between methyl chloride content of 99.4percent.
98.9% With thionyl chloride In N,N-dimethyl-formamide at 90℃; for 4 h; (1) Add 330 g of m-toluic acid to the reaction vessel, add 360 g of thionyl chloride and 5 g of DMF, and stir for 2 h. When there is no obvious gas in the reaction vessel, the temperature is raised to 90 ± 5 ° C. Incubated for 2 h to complete the reaction, and then distilled at 120 ° C excess excess thionyl chloride. M-methyl benzoyl chloride yield of 98.9percent;
Reference: [1] Patent: CN107417518, 2017, A, . Location in patent: Paragraph 0028
[2] Patent: CN105348085, 2016, A, . Location in patent: Paragraph 0026; 0027; 0028; 0029; 0030
[3] Patent: CN107400052, 2017, A, . Location in patent: Paragraph 0016
[4] Canadian Journal of Chemistry, 1963, vol. 41, p. 2962 - 2968
[5] Chemische Berichte, 1879, vol. 12, p. 2300
[6] Chemische Berichte, 1899, vol. 32, p. 1563
[7] Journal of the Chemical Society, 1926, p. 1262
[8] Journal of the Chemical Society, 1896, vol. 69, p. 1311
[9] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1972, vol. 21, p. 558 - 560[10] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1972, vol. 21, p. 599 - 601
[11] Bulletin des Societes Chimiques Belges, 1966, vol. 75, p. 199 - 229
[12] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986, p. 2039 - 2044
[13] Farmaco, 2002, vol. 57, # 9, p. 777 - 782
[14] Tetrahedron, 1968, vol. 24, p. 3829 - 3839
[15] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2746 - 2754
[16] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2843 - 2852
[17] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 11, p. 2457 - 2464
[18] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 7, p. 2045 - 2051
[19] Journal of Medicinal Chemistry, 1983, vol. 26, # 8, p. 1187 - 1192
[20] Journal of Medicinal Chemistry, 1986, vol. 29, # 5, p. 630 - 634
[21] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 202 - 211
[22] Journal of Organometallic Chemistry, 1982, vol. 233, # 2, p. 267 - 274
[23] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3062 - 3070
[24] Doklady Chemistry, 1983, vol. 270, p. 161 - 164[25] Dokl. Akad. Nauk SSSR Ser. Khim., 1983, vol. 270, # 2, p. 333 - 336
[26] Journal of the Indian Chemical Society, 1998, vol. 75, # 9, p. 524 - 525
[27] Pesticide Science, 1994, vol. 41, # 2, p. 139 - 148
[28] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 572 - 576
[29] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
[30] Advanced Synthesis and Catalysis, 2000, vol. 342, # 7, p. 642 - 653
[31] Journal of Medicinal Chemistry, 2003, vol. 46, # 26, p. 5651 - 5662
[32] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 5, p. 763 - 771
[33] Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 1, p. 79 - 84
[34] Journal of the Chinese Chemical Society, 2005, vol. 52, # 5, p. 1021 - 1028
[35] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 4, p. 717 - 721
[36] Journal of Medicinal Chemistry, 2001, vol. 44, # 3, p. 362 - 371
[37] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3420 - 3422
[38] Patent: WO2006/12640, 2006, A2, . Location in patent: Page/Page column 36
[39] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 3118 - 3125
[40] Patent: WO2010/2075, 2010, A1, . Location in patent: Page/Page column 22-23
[41] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 787 - 797
[42] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 14, p. 4273 - 4278
[43] Journal of the Chilean Chemical Society, 2010, vol. 55, # 2, p. 240 - 243
[44] Patent: US2007/155720, 2007, A1, . Location in patent: Page/Page column 18
[45] Letters in Drug Design and Discovery, 2010, vol. 7, # 3, p. 188 - 193
[46] Molecules, 2010, vol. 15, # 6, p. 4267 - 4282
[47] Chemical Biology and Drug Design, 2010, vol. 75, # 5, p. 489 - 493
[48] Journal of Medicinal Chemistry, 2010, vol. 53, # 21, p. 7664 - 7674
[49] Letters in Drug Design and Discovery, 2010, vol. 7, # 4, p. 265 - 268
[50] Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7652 - 7655
[51] Journal of Chemical Research, 2011, vol. 35, # 5, p. 313 - 316
[52] Chemical Biology and Drug Design, 2012, vol. 79, # 6, p. 1018 - 1024
[53] Angewandte Chemie - International Edition, 2011, vol. 50, # 39, p. 9081 - 9084
[54] Journal of the American Chemical Society, 2011, vol. 133, # 38, p. 14952 - 14955
[55] Chemical Communications, 2011, vol. 47, # 44, p. 12074 - 12076
[56] Organic Letters, 2012, vol. 14, # 2, p. 656 - 659
[57] Organic Letters, 2012, vol. 14, # 1, p. 354 - 357
[58] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 231 - 243
[59] Chinese Journal of Chemistry, 2011, vol. 29, # 10, p. 2153 - 2156
[60] Angewandte Chemie - International Edition, 2012, vol. 51, # 9, p. 2247 - 2251
[61] Journal of the American Chemical Society, 2012, vol. 134, # 20, p. 8298 - 8301
[62] Medicinal Chemistry Research, 2012, vol. 21, # 4, p. 511 - 522
[63] Angewandte Chemie - International Edition, 2012, vol. 51, # 29, p. 7318 - 7322
[64] Journal of the American Chemical Society, 2012, vol. 134, # 29, p. 11948 - 11951
[65] Letters in Drug Design and Discovery, 2012, vol. 9, # 8, p. 780 - 788,9
[66] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 22, p. 6974 - 6979,6
[67] Chinese Chemical Letters, 2012, vol. 23, # 11, p. 1233 - 1236,4
[68] Medicinal Chemistry, 2013, vol. 9, # 1, p. 53 - 76
[69] RSC Advances, 2013, vol. 3, # 45, p. 23119 - 23127
[70] Asian Journal of Chemistry, 2014, vol. 26, # 8, p. 2344 - 2350
[71] Journal of the American Chemical Society, 2013, vol. 135, # 14, p. 5308 - 5311
[72] Journal of the Indian Chemical Society, 2013, vol. 90, # 3, p. 381 - 385
[73] Journal of Heterocyclic Chemistry, 2013, vol. 50, # SUPPL.1, p. E39-E42
[74] Asian Journal of Chemistry, 2014, vol. 26, # 8, p. 2362 - 2364
[75] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 231 - 238
[76] Organic and Biomolecular Chemistry, 2013, vol. 11, # 32, p. 5310 - 5324
[77] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8705 - 8711
[78] Bioorganic Chemistry, 2014, vol. 52, p. 1 - 7
[79] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 192 - 194
[80] Angewandte Chemie - International Edition, 2014, vol. 53, # 10, p. 2722 - 2726[81] Angew. Chem., 2014, vol. 126, # 10, p. 2760 - 2764,5
[82] Chemistry - A European Journal, 2014, vol. 20, # 16, p. 4548 - 4553
[83] Organic Letters, 2014, vol. 16, # 15, p. 3904 - 3907
[84] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9788 - 9805
[85] Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 2, p. 449 - 455
[86] Journal of the American Chemical Society, 2014, vol. 136, # 44, p. 15509 - 15512
[87] Journal of Organic Chemistry, 2014, vol. 79, # 22, p. 10988 - 10998
[88] Chemical Communications, 2015, vol. 51, # 1, p. 77 - 80
[89] Organic Letters, 2014, vol. 16, # 24, p. 6412 - 6415
[90] Asian Journal of Chemistry, 2015, vol. 27, # 2, p. 491 - 495
[91] Chemistry--A European Journal, 2015, vol. 21, # 1, p. 205 - 209
[92] Organic Letters, 2015, vol. 17, # 5, p. 1228 - 1231
[93] Chemical Communications, 2014, vol. 50, # 84, p. 12718 - 12721
[94] Chemical Communications, 2015, vol. 51, # 37, p. 7863 - 7866
[95] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9364 - 9368
[96] European Journal of Medicinal Chemistry, 2014, vol. 90, p. 436 - 447
[97] Science China Chemistry, 2015, vol. 58, # 8, p. 1302 - 1309
[98] Medicinal Chemistry, 2015, vol. 11, # 6, p. 567 - 572
[99] Chemistry - A European Journal, 2015, vol. 21, # 41, p. 14342 - 14346
[100] Acta Chimica Slovenica, 2015, vol. 62, # 4, p. 986 - 994
[101] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1484 - 1488
[102] Advanced Synthesis and Catalysis, 2016, vol. 358, # 5, p. 746 - 751
[103] Journal of Molecular Structure, 2016, vol. 1117, p. 8 - 16
[104] Angewandte Chemie - International Edition, 2016, vol. 55, # 13, p. 4308 - 4311[105] Angew. Chem., 2016, vol. 128, p. 4380 - 4383,4
[106] Journal of Organic Chemistry, 2016, vol. 81, # 9, p. 3542 - 3552
[107] Journal of Organic Chemistry, 2016, vol. 81, # 8, p. 3416 - 3422
[108] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2544 - 2546
[109] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 8, p. 1136 - 1141
[110] Chemical Communications, 2016, vol. 52, # 70, p. 10676 - 10679
[111] Chemical Biology and Drug Design, 2016, p. 451 - 459
[112] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5372 - 5376
[113] Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12143 - 12168
[114] Organic Letters, 2016, vol. 18, # 21, p. 5668 - 5671
[115] Journal of the American Chemical Society, 2017, vol. 139, # 5, p. 1762 - 1765
[116] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 15 - 25
  • 4
  • [ 108-38-3 ]
  • [ 99-63-8 ]
  • [ 1711-06-4 ]
YieldReaction ConditionsOperation in experiment
65.7%
Stage #1: at 135℃;
The catalyst dissolved in fresh m-xylene added to the oxidation reactor isN-hydroxyphthalimide,Cobalt naphthenate,Metal phthalocyanine having the structure of the general formula (IV) (R1=H, R2=H, M=Co) and metal porphyrin having the structure of the general formula (III) (R1=R2=R3=H, M1=M2=Mn )mixture,The total concentration is 800ppm and the reaction temperature is 135 °C.The reaction pressure is 0.5 MPa, and the oxygen-containing gas is pure oxygen. The operation procedure is the same as in the first embodiment.The difference is that the conversion of meta-xylene is controlled at 36percent.The content of intermediate methyl benzyl alcohol in the initial steaming tower was controlled to be 0.05percent.The mass percentage of each component obtained by HPLC analysis in the reaction solution is shown in Table 1.The quality of the obtained steaming tower bottom liquid,The contents of the methyl benzoic acid in the mixture of the composition and the initial distillation column are shown in Table 2.The above-mentioned preliminary steaming tower bottom liquid is subjected to rectification,At the top of the column, 376.6 g of m-methylbenzoic acid product with a purity of 99.0percent was obtained.In the column, 1718.8 g of a high-boiling tower liquid having an m-methylbenzoic acid content of 86.5 wtpercent was obtained.Taking thionyl chloride as the acid chloride reagent,The high boiling column liquid is subjected to an acid chlorination reaction,Obtaining an acid chloride reaction solution whose main components are m-methylbenzoyl chloride and isophthaloyl chloride,The reaction end point is the content of m-methylbenzoic acid <0.5 wtpercent.The obtained acid chloride reaction solution is subjected to rectification separation,At the top of the column, 1655.4 g of m-methylbenzoyl chloride and 99.0percent of isophthalic acid were obtained in this order.The acid chloride was 277.9 g. Calculated based on the input meta-xylene,The yield of m-methylbenzoic acid was 17.0percent, and the yield of m-methylbenzoyl chloride was 65.7percent.The yield of isophthalic acid chloride is 8.4percent.The total yield of the three was 91.1percent.
25%
Stage #1: at 156℃;
The catalyst dissolved in fresh m-xylene added to the oxidation reactor is a mixture of MnO2 and Co(Ac)2·4H2O.The compound has a total concentration of 150 ppm and a reaction temperature of 156 ° C.The reaction pressure is 1.0 MPa, and the oxygen-containing gas is pure oxygen.The difference is that the conversion of meta-xylene is controlled to 38percent.The content of intermediate methyl benzyl alcohol in the initial steaming tower was controlled to be 0.05percent.The mass percentage of each component obtained by HPLC analysis in the reaction solution is shown in Table 1.The mass and composition of the obtained preliminary steaming tower bottom liquid and the content of methylbenzoic acid in the initial steaming tower overhead mixture are shown in Table 2.The above-mentioned preliminary steaming tower bottom liquid is subjected to rectification,At the top of the column, 555.2 g of m-methylbenzoic acid product with a purity of 99.0percent was obtained.The column kettle obtained 1552.3 g of a high-boiling tower liquid having an m-methylbenzoic acid content of 84.6 wtpercent.The chlorination reaction is carried out by using sulfoxide as the acyl chloride reagent, and the high boiling column liquid is subjected to an acid chlorination reaction.Obtaining an acid chloride reaction solution whose main components are m-methylbenzoyl chloride and isophthaloyl chloride,The reaction end point is the content of m-methylbenzoic acid <0.5 wtpercent.The obtained acid chloride reaction solution is subjected to rectification separation,At the top of the column, 1461.9 g of m-methylbenzoyl chloride and 99.0percent of isophthalic acid were obtained in this order.The acid chloride was 286.7 g. Calculated based on the input meta-xylene,The yield of m-methylbenzoic acid was 71.8percent, and the yield of m-methylbenzoyl chloride was 25.0percent.The yield of isophthaloyl chloride was 58.0percent, and the total yield of the three was 8.7percent.
Reference: [1] Patent: CN108117486, 2018, A, . Location in patent: Paragraph 18-24; 27; 28
[2] Patent: CN108117486, 2018, A, . Location in patent: Paragraph 18-24; 27; 28
  • 5
  • [ 620-23-5 ]
  • [ 1711-06-4 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 15, p. 3666 - 3669
[2] New Journal of Chemistry, 2017, vol. 41, # 3, p. 931 - 939
[3] Tetrahedron Letters, 2017, vol. 58, # 26, p. 2533 - 2536
  • 6
  • [ 587-03-1 ]
  • [ 1711-06-4 ]
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 26, p. 2533 - 2536
  • 7
  • [ 625-95-6 ]
  • [ 122-04-3 ]
  • [ 636-98-6 ]
  • [ 1711-06-4 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10140 - 10144
  • 8
  • [ 79-37-8 ]
  • [ 99-04-7 ]
  • [ 1711-06-4 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 16, p. 6449 - 6457
[2] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12149 - 12152
  • 9
  • [ 625-95-6 ]
  • [ 100-20-9 ]
  • [ 1711-02-0 ]
  • [ 1711-06-4 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10140 - 10144
  • 10
  • [ 99-04-7 ]
  • [ 98-88-4 ]
  • [ 1711-06-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 6, p. 1129 - 1132[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 6, p. 1275 - 1279
  • 11
  • [ 933-88-0 ]
  • [ 874-60-2 ]
  • [ 1711-06-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 11.2, p. 2139 - 2141[2] Zhurnal Organicheskoi Khimii, 1989, vol. 25, # 11, p. 2372 - 2374
  • 12
  • [ 141-97-9 ]
  • [ 1711-06-4 ]
  • [ 33166-79-9 ]
YieldReaction ConditionsOperation in experiment
17% With sodium hydroxide; ammonium chloride In water; benzene EXAMPLE 6
Preparation of Ethyl 2-Amino-4-(m-Tolyl)-5-Thiazolecarboxylate
To a cold (5° C.) mixture of 137.5 g (1.05 mole) of ethyl acetoacetate, 175 ml. of benzene, 325 ml. of water, and 45.8 ml. of 33percent sodium hydroxide was added simultaneously 221.05 g (1.430 mole) of m-toluoyl chloride and 190 ml. of 33percent sodium hydroxide as described in Example 4.
The aqueous solution of sodium salt of ethyl m-toluoylacetoacetate was stirred with 56.3 g of ammonium chloride overnight and worked up as described in Example 4 to give 38.0 g (17percent) of crude ethyl m-toluoylacetate after a Kugelrohr distillation (95°-98° C.) at 0.05 mm Hg).
17% With sodium hydroxide; ammonium chloride In water; benzene EXAMPLE 6
Preparation of Ethyl 2-Chloro-4-(m-Tolyl)-5-Thiazolecarboxylate
To a cold (5° C.) mixture of 137.5 g (1.05 mole) of ethyl acetoacetate, 175 ml. of benzene, 325 ml. of water, and 45.8 ml. of 33percent sodium hydroxide was added simultaneously 221.05 g (1.430 mole) of m-toluoyl chloride and 190 ml. of 33percent sodium hydroxide as described in Example 4.
The aqueous solution of sodium salt of ethyl m-toluoylacetoacetate was stirred with 56.3 g of ammonium chloride overnight and worked up as described in Example 4 to give 38.0 g (17percent) of crude ethyl m-toluoylacetate after a Kugelrohr distillation (95°-98° C. at 0.05 mm Hg).
Reference: [1] Patent: US4308391, 1981, A,
[2] Patent: US4336389, 1982, A,
  • 13
  • [ 141-97-9 ]
  • [ 1711-06-4 ]
  • [ 33166-79-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1621 - 1630
[2] Chemische Berichte, 1935, vol. 68, p. 227,230
  • 14
  • [ 109-89-7 ]
  • [ 1711-06-4 ]
  • [ 134-62-3 ]
YieldReaction ConditionsOperation in experiment
97.5% With sodium hydroxide In water at 45℃; for 0.05 h; 438.8 g (6 mol) of diethylamine and 1052 g of an aqueous sodium hydroxide solution (19percent) were mixed and stirred.Forming a diethylamine-hydrogen peroxide system, m-methylbenzoyl chloride is an acid chloride system,The two systems were injected into the reactor through a metering pump at a flow rate of 45 ml/min and 35 ml/min, respectively, where n (m-methylbenzoyl chloride): n (diethylamine) = 1:2,Using the microchannel reactor of Figure 2, the temperature is controlled at 45 ° C and the residence time is 180 s.The quantitative collection reaction solution is transferred to a separatory funnel for separation.The organic phase was retained and the aqueous phase was extracted three times with diethyl ether.Drying over anhydrous sodium sulfate, distilling off diethyl ether to give a crude product.After distillation under reduced pressure, fractions of 165 to 175 ° C were collected.A pale yellow liquid was obtained, and the yield of the product calculated by weighing was 97.5percent.Chromatographic detection The purity of the product was 98.3percent.
Reference: [1] Patent: CN107840805, 2018, A, . Location in patent: Paragraph 0032; 0035; 0038; 0041; 0044; 0047-0050; 0053
[2] Chem.Abstr., 1930, vol. 24, p. 94[3] Chem. Zentralbl., 1929, vol. 100, # II, p. 2324
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 9, p. 1225 - 1228
[5] Journal of the American Chemical Society, 2014, vol. 136, # 29, p. 10258 - 10261
  • 15
  • [ 1711-06-4 ]
  • [ 68432-92-8 ]
Reference: [1] Organic and biomolecular chemistry, 2004, vol. 2, # 12, p. 1732 - 1741
  • 16
  • [ 393-52-2 ]
  • [ 1711-06-4 ]
  • [ 80277-41-4 ]
  • [ 5955-74-8 ]
Reference: [1] Patent: US6359156, 2002, B1, . Location in patent: Page column 10
  • 17
  • [ 1711-06-4 ]
  • [ 22071-22-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 1974, vol. 9, # 4, p. 381 - 389
  • 18
  • [ 1711-06-4 ]
  • [ 24188-72-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2746 - 2754
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1711-06-4 ]

Aryls

Chemical Structure| 73291-09-5

[ 73291-09-5 ]

4-(Chloromethyl)benzaldehyde

Similarity: 0.88

Chemical Structure| 1711-11-1

[ 1711-11-1 ]

3-Cyanobenzoyl chloride

Similarity: 0.81

Chemical Structure| 6068-72-0

[ 6068-72-0 ]

4-Cyanobenzoyl chloride

Similarity: 0.81

Chemical Structure| 4659-45-4

[ 4659-45-4 ]

2,6-Dichlorobenzoyl Chloride

Similarity: 0.74

Chemical Structure| 42728-62-1

[ 42728-62-1 ]

4-Chloromethylbenzophenone

Similarity: 0.73

Chlorides

Chemical Structure| 73291-09-5

[ 73291-09-5 ]

4-(Chloromethyl)benzaldehyde

Similarity: 0.88

Chemical Structure| 1711-11-1

[ 1711-11-1 ]

3-Cyanobenzoyl chloride

Similarity: 0.81

Chemical Structure| 6068-72-0

[ 6068-72-0 ]

4-Cyanobenzoyl chloride

Similarity: 0.81

Chemical Structure| 4659-45-4

[ 4659-45-4 ]

2,6-Dichlorobenzoyl Chloride

Similarity: 0.74

Chemical Structure| 42728-62-1

[ 42728-62-1 ]

4-Chloromethylbenzophenone

Similarity: 0.73

Acyl Chlorides

Chemical Structure| 1711-11-1

[ 1711-11-1 ]

3-Cyanobenzoyl chloride

Similarity: 0.81

Chemical Structure| 6068-72-0

[ 6068-72-0 ]

4-Cyanobenzoyl chloride

Similarity: 0.81

Chemical Structure| 4659-45-4

[ 4659-45-4 ]

2,6-Dichlorobenzoyl Chloride

Similarity: 0.74

Chemical Structure| 393-52-2

[ 393-52-2 ]

2-Fluorobenzoyl chloride

Similarity: 0.69

Chemical Structure| 72482-64-5

[ 72482-64-5 ]

2,4-Difluorobenzoyl chloride

Similarity: 0.68