[ CAS No. 3366-95-8 ] {[proInfo.proName]}

Name: 3366-95-8|1-(2-Methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol|98%
Brand: Ambeed
SKU: A445585
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2D 3D

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Quality Control of [ 3366-95-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3366-95-8 ]

SDS Specification

Alternatived Products of [ 3366-95-8 ]

Product Details of [ 3366-95-8 ]

CAS No. :	3366-95-8	MDL No. :	MFCD00864656
Formula :	C₇H₁₁N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KPQZUUQMTUIKBP-UHFFFAOYSA-N
M.W :	185.18	Pubchem ID :	71815
Synonyms :	PM-185184;RP-14539;Sindose, Secnil.;Secnidazole, trade name: Flagentyl, Secnol, Deprozol, Sabima;SYM-1219

Calculated chemistry of [ 3366-95-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.57
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.05
TPSA :	83.87 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.58
Log Po/w (XLOGP3) :	0.22
Log Po/w (WLOGP) :	0.48
Log Po/w (MLOGP) :	-0.84
Log Po/w (SILICOS-IT) :	-1.48
Consensus Log Po/w :	-0.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.21
Solubility :	11.3 mg/ml ; 0.0612 mol/l
Class :	Very soluble
Log S (Ali) :	-1.54
Solubility :	5.33 mg/ml ; 0.0288 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.45
Solubility :	66.5 mg/ml ; 0.359 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.83

Safety of [ 3366-95-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3366-95-8 ]

* 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 [ 3366-95-8 ]
Downstream synthetic route of [ 3366-95-8 ]

[ 3366-95-8 ] Synthesis Path-Upstream 1~1

1
[ 19686-73-8 ]
[ 696-23-1 ]
[ 3366-95-8 ]

Yield	Reaction Conditions	Operation in experiment
89.1%	With potassium carbonate In acetone at 70℃; for 5 h;	In a 10L of Glass Reactor add 2-methyl-5-nitroimidazole, 1-bromo-2-propanol, potassium carbonate, acetone with molar ratio of 1 :3 :3 :20. Wherein, the mass of 2-methyl-5-nitroimidazole mass is 635g,, the mass of 1-bromo-2-propanol is 2070g, , the mass of Potassium carbonate is 2114g and volume of acetone is 7.1L. Under stirring, the reaction was refluxed for 5 hours and the reaction temperature was at 70 ° C; According to TLC analysis(Expand Condition: GF254 silica gel plate, developing solvent chloroform: ethanol = 85: 15) The end point ofthe reaction to obtain a reaction mixture A. A recovered acetone from the reaction mixture to A obtain a reaction mixture B; in reaction mixture B add 9L of water and reaction mixture B through cooled to 0 °C,centrifuged wet product; Clean water and stir 3 hours of The wet product with a temperatureof 1 ° C again Again centrifuged toobtain secnidazole crude. Thecrude product was added into 5L ofreactor then 40percent ethanol 3L was added and Activated Carbon 30g; It was heated upto 70 ° C, under reflux to dissolve and filtered to obtain a filtrate;The filtrate was cooled down to 0 ° C and crystallization three hours; Centrifugation, and dried in vacuum at 40 ° C to obtain Secnidazole. After weighing and calculation, the obtained quality of secnidazoles 820g, a total yield of 89.1percent.

Reference： [1] Patent: CN103772289, 2016, B, . Location in patent: Paragraph 0036-0042

[ 3366-95-8 ] Synthesis Path-Downstream 1~88

1
[ 108-24-7 ]
[ 3366-95-8 ]
Acetic acid 1-methyl-2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl ester [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1987,vol. 70,p. 171 - 174

2
[ 3366-95-8 ]
N-(2-hydroxypropyl)-5-methyl-1,2,4-oxadiazole-3-carboxamide [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1987,vol. 70,p. 171 - 174

3
[ 7205-98-3 ]
[ 3366-95-8 ]
1-[2-methyl-5-nitro-4-(phenylsulfonyl)methyl-1H-imidazol-1-yl]propan-2-ol [ No CAS ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3639 - 3646
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 653 - 659

4
[ 7569-26-8 ]
[ 3366-95-8 ]
1-[2-methyl-5-nitro-4-(tosylmethyl)-1H-imidazol-1-yl]propan-2-ol [ No CAS ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3639 - 3646
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 653 - 659

5
[ 5943-04-4 ]
[ 3366-95-8 ]
1-[4-(4-chlorophenylsulfonyl)methyl-2-methyl-5-nitro-1H-imidazol-1-yl]propan-2-ol [ No CAS ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3639 - 3646
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 653 - 659

6
[ 54091-06-4 ]
[ 3366-95-8 ]
1-[4-(4-bromophenylsulfonyl)methyl-2-methyl-5-nitro-1H-imidazol-1-yl]propan-2-ol [ No CAS ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 3639 - 3646
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 653 - 659

7
[ 3366-95-8 ]
5-[3-(2-hydroxy-propyl)-2-methyl-3<i>H</i>-imidazol-4-ylazo]-quinolin-8-ol [ No CAS ]

Reference： [1]Il Farmaco,2004,vol. 59,p. 843 - 846

8
[ 10025-99-7 ]
[ 3366-95-8 ]
[ 84431-19-6 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1985,p. 795 - 802

9
[ 433-13-6 ]
[ 3366-95-8 ]
[ 1146349-32-7 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 653 - 659

10
[ 15690-25-2 ]
[ 3366-95-8 ]
[ 1326302-72-0 ]

Yield	Reaction Conditions	Operation in experiment
72.9%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

11
[ 1866-39-3 ]
[ 3366-95-8 ]
[ 1326302-64-0 ]

Yield	Reaction Conditions	Operation in experiment
62.9%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

12
[ 20595-30-6 ]
[ 3366-95-8 ]
[ 1326302-58-2 ]

Yield	Reaction Conditions	Operation in experiment
66.2%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

13
[ 459-32-5 ]
[ 3366-95-8 ]
[ 1326302-61-7 ]

Yield	Reaction Conditions	Operation in experiment
66.7%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

14
[ 1615-02-7 ]
[ 3366-95-8 ]
[ 1326302-62-8 ]

Yield	Reaction Conditions	Operation in experiment
56.1%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

15
[ 1552-96-1 ]
[ 3366-95-8 ]
[ 1326302-68-4 ]

Yield	Reaction Conditions	Operation in experiment
57.1%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

16
[ 20595-45-3 ]
[ 3366-95-8 ]
[ 1326302-69-5 ]

Yield	Reaction Conditions	Operation in experiment
56.9%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

17
[ 51557-26-7 ]
[ 3366-95-8 ]
[ 1326302-71-9 ]

Yield	Reaction Conditions	Operation in experiment
63.4%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

18
[ 451-69-4 ]
[ 3366-95-8 ]
[ 1326302-54-8 ]

Yield	Reaction Conditions	Operation in experiment
65.6%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

19
[ 13026-12-5 ]
[ 3366-95-8 ]
[ 1326302-70-8 ]

Yield	Reaction Conditions	Operation in experiment
68.7%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

20
[ 14473-91-7 ]
[ 3366-95-8 ]
[ 1326302-59-3 ]

Yield	Reaction Conditions	Operation in experiment
67.2%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

21
[ 1200-07-3 ]
[ 3366-95-8 ]
[ 1326302-63-9 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

22
[ 88241-65-0 ]
[ 3366-95-8 ]
[ 1326302-66-2 ]

Yield	Reaction Conditions	Operation in experiment
58.7%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

23
[ 6099-03-2 ]
[ 3366-95-8 ]
[ 1326302-57-1 ]

Yield	Reaction Conditions	Operation in experiment
59.2%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

24
[ 6099-04-3 ]
[ 3366-95-8 ]
[ 1326302-60-6 ]

Yield	Reaction Conditions	Operation in experiment
72.9%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

25
[ 7345-79-1 ]
[ 3366-95-8 ]
[ 1326302-56-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

26
[ 6272-45-3 ]
[ 3366-95-8 ]
[ 1326302-67-3 ]

Yield	Reaction Conditions	Operation in experiment
53.36%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

27
[ 621-82-9 ]
[ 3366-95-8 ]
[ 1326302-53-7 ]

Yield	Reaction Conditions	Operation in experiment
60.9%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

28
[ 830-09-1 ]
[ 3366-95-8 ]
[ 1326302-65-1 ]

Yield	Reaction Conditions	Operation in experiment
67.8%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 50 - 60℃; for 24h;	General procedure: Equimolar amount of <strong>[3366-95-8]secnidazole</strong> (1.0 mmol) and cinnamic acid (1.0 mmol) were dissolved in dichloromethane, DCC (1.5 mmol) and DMAP (0.5 mmol) as catalyst and stirred at 50-60 C for 24 h. The reaction mixture was extracted with ethyl acetate and saturated sodium bicarbonate, respectively. Then, the organic layer was collected and crystallized to get the product (Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 4513 - 4519

29
[ 3366-95-8 ]
[ 1393310-68-3 ]

Reference： [1]Journal of Chemical Crystallography,2011,vol. 41,p. 1360 - 1364

30
zinc(II) nitrate hexahydrate [ No CAS ]
[ 7732-18-5 ]
[ 3366-95-8 ]
[Zn(secnidazole)3(NO₃)][NO₃]*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C21H33N11O15Zn·2H2O: C, 32.30; H, 4.78; N, 19.73. Found: C, 32.29; H, 4.30; N, 19.56%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

31
nickel(II) chloride hexahydrate [ No CAS ]
[ 7732-18-5 ]
[ 3366-95-8 ]
[Ni(secnidazole)2(H₂O)2Cl₂]*5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C14H22Cl2N6O6Ni·5H2O: C, 28.50; H, 5.47; N, 14.24. Found: C, 28.96; H, 5.12; N, 14.72%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

32
[ 6018-89-9 ]
[ 3366-95-8 ]
[Ni₂(secnidazole)4(μ₂-O₂C2H₃)₄] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

33
nickel(II) nitrate hexahydrate [ No CAS ]
[ 7732-18-5 ]
[ 3366-95-8 ]
[Ni(secnidazole)3(NO₃)][NO₃]*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C21H33N11O15Ni·2H2O: C, 32.58; H, 4.82; N, 19.90. Found: C, 32.31; H, 4.84; N, 19.30%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

34
[ 7732-18-5 ]
[ 3366-95-8 ]
[ 7789-45-9 ]
[Cu(secnidazole)₂Br₂]*0.5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C14H22Br2N6O6Cu·0.5H2O: C, 27.90; H, 3.85; N, 13.94. Found: C, 27.22; H, 3.21; N, 14.71%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

35
[ 7732-18-5 ]
[ 3366-95-8 ]
cobalt(II) bromide [ No CAS ]
[Co(secnidazole)₂Br₂]*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C14H22N6O6Br2Cu*H2O: C, 33.51; H, 4.39; N, 16.65. Found: C, 34.02; H, 4.24; N, 16.81%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

36
[ 7732-18-5 ]
[ 6147-53-1 ]
[ 3366-95-8 ]
[Co₂(secnidazole)₆(O₂C₂H₃)₂(μ₂-O₂ H₅C₃)₂]·H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C50H78N18O26Co2·H2O: C, 40.49; H, 5.44; N, 17.00. Found: C, 40.08; H, 5.28; N, 17.46%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

37
copper nitrate hemi(pentahydrate) [ No CAS ]
[ 64-17-5 ]
[ 3366-95-8 ]
[Cu(secnidazole)3(NO₃)][NO₃]*EtOH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C21H33N11O15Cu·CH3CH2OH: C, 35.00; H, 4.98; N, 19.52. Found: C, 34.66; H, 5.03; N, 19.08%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

38
[ 6046-93-1 ]
[ 3366-95-8 ]
[ 1270038-75-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C22H34N6O14Cu2: C, 36.02; H, 4.67; N, 11.46. Found: C, 36.50; H, 4.49; N, 11.49%. Crystals suitable for X-ray diffraction were grown in a saturated ethanol solution at 298 K.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

39
cobalt(II) chloride hexahydrate [ No CAS ]
[ 3366-95-8 ]
[ 1429662-20-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. C21H37Cl2N9O10Co: C, 35.86; H, 5.02; N, 17.92. Found: C, 36.29; H, 4.69; N, 17.47%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

40
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 3366-95-8 ]
[ 1429662-28-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C21H35N11O16Co: C, 33.34; H, 4.66; N, 20.37. Found: C, 33.78; H, 5.05; N, 20.24%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

41
[ 3366-95-8 ]
[ 7646-85-7 ]
[ 1429662-21-4 ]

Yield	Reaction Conditions	Operation in experiment
46%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C21H35Cl2N9O10Zn: C, 35.53; H, 4.97; N, 17.76. Found: C, 35.22; H, 4.53; N, 17.26%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

42
copper(II) choride dihydrate [ No CAS ]
[ 3366-95-8 ]
[ 1429662-19-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol; for 4h;Reflux;	General procedure: One mol equiv. of the corresponding transition metal salt was added to a solution of three mol equiv of <strong>[3366-95-8]secnidazole</strong> in 20 mL of ethanol (reagent grade) with constant stirring under reflux for 4 h, upon which the precipitate formed was collected by filtration. The remaining solution was concentrated and portions of hexane were added to further precipitate the product which was again collected by filtration. Both solids were combined and washed with portions of hexane and MeOH and dried overnight under vacuum resulting in microcrystalline product. Elemental Anal. Calc. for C14H22N6O6Cl2Cu: C, 33.51; H, 4.39; N, 16.65. Found: C, 34.02; H, 4.24; N, 16.81%.

Reference： [1]Inorganica Chimica Acta,2013,vol. 397,p. 94 - 100

43
[ 591-31-1 ]
[ 3366-95-8 ]
[ 1448528-46-8 ]

Yield	Reaction Conditions	Operation in experiment
66.1%	With sodium methylate; In methanol; dimethyl sulfoxide; at 20℃;	General procedure: To a solution of the <strong>[3366-95-8]1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol</strong> (12 mmol) in DMSO (6 mL) at room temperature were added aromatic aldehydes 1-21 (16mmol) and sodium methoxide in methanol (12.8 mmol). The reaction mixture was stirred at room temperature until TLC (VEtOAc/Vhexanes 1:2) indicated reaction completion(generally4-5h) and poured into ice-water (250mL). Theprecipitate formed was collected, washed three times with distilled water, and dried under vacuum. The crude products were purified by recrystallization with ethanol, ethyl acetate and acetone (1:1:0.05) washed by ice-water (25mL) for three times to give a pure product.