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Quality Control of Clotrimazole Impurity F Purity: 98% SDS Specification

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Product Details of Clotrimazole Impurity F

CAS No. :	15469-97-3
Formula :	C₂₂H₁₈N₂
M.W :	310.39
SMILES Code :	N1(C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C=CN=C1
Synonyms :	1-Tritylimidazole
MDL No. :	MFCD00229427
InChI Key :	NPZDCTUDQYGYQD-UHFFFAOYSA-N
Pubchem ID :	618231

Safety of Clotrimazole Impurity F

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Clotrimazole Impurity F

* 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 [ 15469-97-3 ]
Downstream synthetic route of [ 15469-97-3 ]

[ 15469-97-3 ] Synthesis Path-Upstream 1~1

1
[ 15469-97-3 ]
[ 121816-82-8 ]
[ 87941-55-7 ]

References: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 95 - 99.
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 95 - 99.

[ 15469-97-3 ] Synthesis Path-Downstream 1~41

1
[ 288-32-4 ]
[ 95953-45-0 ]
[ 15469-97-3 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 7023 - 7027.

2
[ 288-32-4 ]
[ 76-83-5 ]
[ 15469-97-3 ]

Yield	Reaction Conditions	Operation in experiment
95.6%		Compound XIII (880g, 12.9mol, 1.0eq.) In the autoclave 50L, 12L DMF were dissolved, cooled To below 0 °C, triethylamine (1308g, 12.9mol, 1.0eq. ) The reaction was kept 30min, 0 ° C solution of the following threePhenyl chloride (3605.0g, 12.9mol, 1.0eq. ) In DMF (16L), drops Bi, 15 ° C overnight with stirring 16 h. Thereaction mixture was poured into water, large amount of solid precipitated, suction filtered, the filter cake washedwith water, drained, dried to obtain compound XIV-1 White The solid 3835.1g, Yield: 95.6percent.
91%		1-trityl-midazol (Compound 28, Scheme 19) was prepared by adding Et3N (5.1 ml, 36.7 mmol) at 0° C. to a stirred solution of the imidazole Compound 27 (2.5 grams, 36.7 mmol) dissolved in 75 ml DMF. After 30 minutes of stirring, trityl-chloride (10.3 grams, 36.7 mmol) dissolved in DMF (45 ml) was added slowly to the reaction mixture, and the reaction mixture was allowed to reach room temperature while stirred continuously for over night. Thereafter the reaction mixture was quenched with cold water (1 L) to precipitate a solid, which was collected by filtration and recrystallized from hexane/DCM to afford Compound 28 as a white solid (91percent yield).1H NMR (500 MHz, CDCl3)-delta: 7.47 (s, 1H), 7.33-7.30 (m, 9H), 7.16-7.12 (m, 6H), 7.07 (s, 1H), 6.83 (s, 1H).
90%	With ammonium chloride; triethylamine; In dichloromethane;	Example 22 Synthesis of 1-tritylimidazole (5) To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol.) in 50 ml dry methylene chloride. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight. The reaction mixture was then washed with 20 ml of a 10percent solution of ammonium chloride, then with 20 ml of distilled water. The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid. Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90percent after recrystallization). m.p. 214° C.; 1H NMR (200 MHz, CDCl3) delta7.43 (m, 1H, NCHN), 7.3-7.4 (m, 9H, 3C6H5), 7.1-7.2 (m, GH, 3C6H5), 7.0 (m, 1H, Ph3CNCH=CH), 6.81 (m, 1H, Ph3CNCH=CH); 13C NMR (50 MHz, CDCl3) delta142.3, 139.0, 129.6, 128.2, 128.3, 121.6.

90%	With ammonium chloride; triethylamine; In dichloromethane;	Example 22 Synthesis of 1-tritylimidazole (5) STR73 To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol.) in 50 ml dry methylene chloride. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight. The reaction mixture was then washed with 20 ml of a 10percent solution of ammonium chloride, then with 20 ml of distilled water. The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid. Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90percent after recrystallization). m.p. 214° C.; 1 H NMR (200 MHz, CDCl3) delta 7.43 (m, 1H, NCHN), 7.3-7.4 (m, 9H, 3xC6 H5), 7.1-7.2 (m, 6H, 3xC6 H5), 7.0 (m, 1H, Ph3 CNCH=CH), 6.81 (m, 1H, Ph3 CNCH=CH); 13 C NMR (50 MHz, CDCl3) delta 142.3, 139.0, 129.6, 128.2, 128.3, 121.6.
90%	With ammonium chloride; triethylamine; In dichloromethane;	Example 22 Synthesis of 1-tritylimidazole (5) STR70 To a solution of trityl chloride (5.58 g, 20.0 mmol.) in dry methylene chloride (100 ml) cooled down to 0° C. and stirred under Ar, was added dropwise over 1.5 hours a solution of imidazole (1.36 g, 20.0 mmol.) and triethylamine (2.7 mml, 20 mmol) in 50 ml dry methylene chloride. At the end of the addition, the reaction mixture was allowed to warm up to room temperature and stirred under Ar at that temperature overnight. The reaction mixture was then washed with 20 ml of a 10percent solution of ammonium chloride, then with 20 ml of distilled water. The organic phase was dried over magnesium sulfate and evaporated in vacuo to yield quantitatively a white solid. Recrystallization from methylene chloride/hexanes yielded 5.60 g of (5) (yield=90percent after recrystallization). m.p. 214° C.; 1 H NMR (200 MHz, CDCl3) delta7.43 (m, 1H, NCHN), 7.3-7.4 (m, 9H, 3C6 H5), 7.1-7.2 (m, 6H, 3C6 H5), 7.0 (m, 1H, Ph3 CNCH=CH), 6.81 (m, 1H, Ph3 CNCH=CH); 13 C NMR (50 MHz, CDCl3) delta142.3, 139.0, 129.6, 128.2, 128.3, 121.6.
	In 5,5-dimethyl-1,3-cyclohexadiene; water; ethyl acetate;	EXAMPLE VII 1-TRITYLIMIDAZOLE To a stirred solution of 23.5 g (0.35 mole) of imidazole in 425 mL of ethyl acetate was added 48.0 g (0.32 mole) of triphenylmethyl chloride. The mixture was stirred for 20 hours and then 500 mL of water was added. After being stirred for an additional 2 hours, the mixture was filtered. The ethyl acetate layer was separated, dried (MgSO4) and concentrated. Recrystallization of the residue from xylene gave 41 g of white crystals, mp 222°-225° C..

References: [1]Patent: CN104086553,2016,B .Location in patent: Paragraph 0065-0068.
[2]Patent: US2010/16610,2010,A1 .Location in patent: Page/Page column 28.
[3]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 253 - 256.
[4]Tetrahedron,1999,vol. 55,p. 4109 - 4122.
[5]Patent: US6476216,2002,B1 .
[6]Patent: US6160109,2000,A .
[7]Patent: US5734041,1998,A .
[8]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 903 - 906.
[9]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 2 - 6.
[10]European Journal of Organic Chemistry,2011,p. 6092 - 6099.
[11]Heterocycles,1985,vol. 23,p. 2895 - 2906.
[12]Arzneimittel-Forschung/Drug Research,1992,vol. 42,p. 832 - 835.
[13]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 857 - 860.
[14]Patent: US5039691,1991,A .
[15]ChemMedChem,2010,vol. 5,p. 899 - 910.

3
[ 15469-97-3 ]
[ 121512-57-0 ]
5-Methanesulfonyl-3,6,11,11b-tetraaza-cyclopenta[a]anthracen-4-ylamine [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 194 - 199.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 224 - 229.

4
[ 15469-97-3 ]
[ 882-33-7 ]
[ 123940-53-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 1139 - 1145.
[2]Tetrahedron,1999,vol. 55,p. 4109 - 4122.

5
[ 15469-97-3 ]
[ 74-88-4 ]
[ 90408-25-6 ]
[ 23593-68-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 481 - 486.

6
[ 15469-97-3 ]
[ 16681-56-4 ]

References: [1]Synthetic Communications,1989,vol. 19,p. 2551 - 2566.

7
[ 15469-97-3 ]
[ 3034-62-6 ]

References: [1]Synthetic Communications,1989,vol. 19,p. 2551 - 2566.

8
[ 15469-97-3 ]
[ 527-73-1 ]

References: [1]Inorganic Chemistry Communications,2017,vol. 78,p. 32 - 36.
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 253 - 256.

9
[ 15469-97-3 ]
[ 121816-82-8 ]
[ 87941-55-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 95 - 99.
[2]Journal of the Chemical Society. Perkin transactions I,1989,p. 95 - 99.

10
[ 15469-97-3 ]
diphenyl-<4-(imidazol-1-yl)>phenylmethane [ No CAS ]

References: [1]Heterocycles,1981,vol. 15,p. 943 - 945.

11
[ 15469-97-3 ]
2-chloro-1-trityl-1H-imidazole [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1994,vol. 131,p. 590 - 599.
[2]Journal of the American Chemical Society,2009,vol. 131,p. 10368 - 10369.

12
[ 15469-97-3 ]
2-azido-1-trityl-1H-imidazole [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1994,vol. 131,p. 590 - 599.

13
[ 15469-97-3 ]
[ 29976-53-2 ]
[ 873215-54-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 146 - 149.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3860 - 3863.

14
[ 922163-66-4 ]
[ 15469-97-3 ]
2,3,5-tris-benzyloxy-4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-(1-trityl-1<i>H</i>-imidazol-2-yl)-pentan-1-ol [ No CAS ]
[ 922163-68-6 ]

Yield	Reaction Conditions	Operation in experiment
18%; 53%		Compounds 6 and 7: To a solution of tritylimidazole (2.67 g, 8.6 mmol) in THF (85 ml) cooled to -20 C a stock 1.6 M solution n-butyl lithium in hexanes (5.13 ml, 8.2 mmol) was added dropwise. The resulting wine red coloured solution was allowed to warm up to RT and stirred for 30 min. The solution was then cooled to -78 C and a solution of aldehyde (4.17 g, 7.8 mmol) in THF (15ml) was added dropwise. The resulting solution was stirred for 30 min and then allowed to warm to RT in 30 min. The reaction was quenched by addition of ammonium chloride solution and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate once more. The combined organic layer was dried and evaporated. The residue was purified by flash column chromatography in PE-EA gradient 10-20-30percent to give 1.18 g (1.4 mmol, 18percent) of 6 (Rf = 0.55 PE- EA 20percent) and 3.48 g (4.13 mmol, 53percent) of 7 (Rf = 0.4 PE-EA 20percent) .6: [?]D = -10.5 c 1.24 CHCl3HRMS: Positive mode, m/z = 845.4344; expected for C54H6IN2O5Si [M+H]+ = 845.4350.?H (500 MHz) : 0.0 and 0.02 (6H, 2s, -Si (CH3) C (CH3) 3) , 0.89 (9H, s, -Si(CH3)C(CH3)S) , 2.94 (IH, dd, J4, 5 = 6.5 Hz, J4/3 = 4.1 Hz, H-4) , 3.1 (IH, bs, 2-OH) , 3.14 (IH, dd, J6a,5 = 5.4, Jea,6b = 10.2 Hz, H-6a) , 3.37 (IH, dd, J6b,5 = 3 Hz, H- 6b) , 3.8 (IH, dd, J3, 2 = 3.2 Hz, H-3) , 3.93 (IH, ddd, H-5) , 3.97 and 4.41 (2H, AB spectrum, Jgem = 11.5 Hz, PhCH2O-) , 4.3 (IH, bs, H-2) , 4.33 (2H, s, PhCH2O-) , 4.71 and 4.93 (2H, AB spectrum, Jgem = 11.2 Hz, PhCH2O-) , 6.78 (IH, m) , 7.02 (2H, m) , 7.13-7.4 (28H, m) .?c (125 MHz) : -4.4, 18.2, 26.1, 66.6 (C-2) , 72.8 (C-6) , 72.9 (C-5) , 73.2, 73.8, 74.4, 75.3, 78.8 (C-3) , 81.7 (C-4) , 122.2, 126.08, 127.06, 127.3, 127.4, 127.8, 128.1, 128.3, 128.5, 130, 138.6, 138.8, 138.9, 142.9, 150.7.7: [?]D = -67.5 c 1.34 CHCl3HRMS: Positive mode, m/z = 845.4344; expected for C54H6IN2O5Si [M+H]+ = 845.4350.?H (500 MHz) : -0.09 and 0.0 (6H, 2s, -Si (CH3) C (CH3) 3) , 0.82 (9H, s, -Si (CH3) C (CH3) 3) , 3.52 (IH, dd, J6a,5 = 6.5 Hz, J6a,6b = 10.4 Hz, H-6a) , 3.73 (IH, dd, J4, 5 = 7.3, J4, 3 = 2.6 Hz, H- A) 1 3.78 (IH, dd, J6b,5 = 2.2 Hz, H-6b) , 4.12 (IH, ddd, J5, 4 =6.7 Hz, H-5) , 4.24 (IH, dd, J3, 2 = 8.7 Hz, H-3) , 4.27 and 4.57 (2H, AB spectrum, Jgem = 12.4 Hz, PhCH2O-) , 4.41 (2H, s, PhCH2O-) , 4.48 and 4.6 (2H, AB spectrum, Jgem = 10.7 Hz, PhCH2O-) , 4.5 (IH, dd, J2, 0H = 4 Hz, H-2) , 6.79 (IH, m) , 6.85-7.4 (31H, m) .?c (125 MHz) : -4.7, 18.2, 26, 65.9 (C-2) , 72.6 (C-5) ,73.1, 73.2 (C-6) , 73.8, 75.5, 79.6 (C-4) , 80.13 (C-3) , 122.3, 125.9, 126.17, 126.5, 127, 127.2, 127.6, 127.8,127.9, 128.1, 128.4, 128.6, 130, 130.2, 138.7, 139, 139.3, 141, 142.5, 150.2 (C-I) .

References: [1]Patent: WO2008/59267,2008,A1 .Location in patent: Page/Page column 21-23.
[2]Journal of the American Chemical Society,2006,vol. 128,p. 16484 - 16485.

15
[ 15469-97-3 ]
5,5-diphenyl-5H-imidazo[2,1-a]isoindole [ No CAS ]

References: [1]Synthesis,2007,p. 529 - 540.

16
[ 15469-97-3 ]
[ 399508-62-4 ]

References: [1]European Journal of Organic Chemistry,2001,p. 4111 - 4125.

17
[ 15469-97-3 ]
[ 399508-40-8 ]

References: [1]European Journal of Organic Chemistry,2001,p. 4111 - 4125.

18
[ 15469-97-3 ]
[ 399508-52-2 ]

References: [1]European Journal of Organic Chemistry,2001,p. 4111 - 4125.

19
[ 15469-97-3 ]
[ 399508-61-3 ]

References: [1]European Journal of Organic Chemistry,2001,p. 4111 - 4125.

20
[ 15469-97-3 ]
[ 399508-41-9 ]

References: [1]European Journal of Organic Chemistry,2001,p. 4111 - 4125.

21
[ 15469-97-3 ]
[ 399508-53-3 ]

References: [1]European Journal of Organic Chemistry,2001,p. 4111 - 4125.

22
[ 15469-97-3 ]
[ 162438-96-2 ]

References: [1]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 427 - 436.
[2]Tetrahedron Letters,1995,vol. 36,p. 1085 - 1088.

23
[ 15469-97-3 ]
Phenyl-methanesulfonic acid (1S,2R,3R,4R)-2,3-bis-benzyloxy-1-benzyloxymethyl-4-hydroxy-4-(1-trityl-1H-imidazol-2-yl)-butyl ester [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 427 - 436.
[2]Tetrahedron Letters,1995,vol. 36,p. 1085 - 1088.

24
[ 15469-97-3 ]
cis-1-(4-chlorophenyl)-3-(1-trityl-2-imidazolyl)-2-propen-1-one [ No CAS ]