[ CAS No. 21304-39-2 ] {[proInfo.proName]}

Name: 21304-39-2|1-(3,4-Diaminophenyl)ethanone|95%
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SKU: A892625
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Quality Control of [ 21304-39-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 21304-39-2 ]

Product Details of [ 21304-39-2 ]

CAS No. :	21304-39-2	MDL No. :	MFCD12031488
Formula :	C₈H₁₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FFVSGYAQHXJFAL-UHFFFAOYSA-N
M.W :	150.18	Pubchem ID :	432723
Synonyms :

Calculated chemistry of [ 21304-39-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.45
TPSA :	69.11 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) :	-6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.84
Log Po/w (XLOGP3) :	0.34
Log Po/w (WLOGP) :	1.07
Log Po/w (MLOGP) :	0.51
Log Po/w (SILICOS-IT) :	0.71
Consensus Log Po/w :	0.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.32
Solubility :	7.14 mg/ml ; 0.0475 mol/l
Class :	Very soluble
Log S (Ali) :	-1.36
Solubility :	6.63 mg/ml ; 0.0441 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.0
Solubility :	1.51 mg/ml ; 0.0101 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 21304-39-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 21304-39-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 21304-39-2 ]

[ 21304-39-2 ] Synthesis Path-Downstream 1~88

1
[ 21304-39-2 ]
[ 146519-40-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1942,vol. 553,p. 250,257

2
[ 21304-39-2 ]
[ 13535-47-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1942,vol. 553,p. 250,257

3
[ 1432-42-4 ]
[ 21304-39-2 ]

Yield	Reaction Conditions	Operation in experiment
		142a 1- (3, 4-diaminophenyl) ethanone [003741 To a solution of 4-methylcarbonyl-2-nitro-benzenamine (500 mg, 2.775 mmol) in EtOAc (16 mL) was added SnCl2. 2H2O (3. 130 g, 13.88 mmol). The reaction mixture was refluxed for 2.5 h, cooled to rt, and diluted with H20 (130 mL). The pH of the mixture was adjusted to 7-8 by addition of saturated NaHC03 solution and the aqueous phase was extracted with EtOAc (2 x 120 mL). The combined organic extracts were washed with brine (2 x 60 mL) and dried over MgSO4. After the removal of the solvent under vacuum, 142a was obtained as a red orange solid (418 mg).
1.1 g	With palladium 10% on activated carbon; hydrogen; In ethanol; water; at 20℃; for 20h;Inert atmosphere;	A flask charged with a solution of intermediate 165.1 (1.46g) in EtOH/H2O (270mL/13mL) was evacuated and backfilled with argon three times. Pd/C (10%, 216mg) was added and the flask was evacuated and backfilled with argon three times then with hydrogen twice. The reaction mixture was stirred at RT under hydrogen for 20h, filtrated over celite and the celite was washed with EtOH. The filtrate was evaporated and dried in vacuo to afford 1.1 g of black solid. LC-MS (B): tR = 0.32min; [M+H]+: 151.20.
1.1 g	With palladium 10% on activated carbon; hydrogen; In ethanol; water; at 20℃; for 20h;	A flask charged with a solution of intermediate 165.1 (1.46 g) in EtOH/ H2O (270 mL/13 mL) was evacuated and backfilled with argon three times. Pd/C (10%, 216 mg) was added and the flask was evacuated and backfilled with argon three times then with hydrogen twice. The reaction mixture was stirred at RT under hydrogen for 20 h, filtrated over celite and the celite was washed with EtOH. The filtrate was evaporated and dried in vacuo to afford 1.1 g of black solid. LC-MS (B): tR=0.32 min; [M+H]+: 151.20.

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 1011 - 1018
[2]Justus Liebigs Annalen der Chemie,1942,vol. 553,p. 250,257
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 574 - 577
[4]Journal of Medicinal Chemistry,1998,vol. 41,p. 1777 - 1788
[5]Patent: WO2005/70920,2005,A1 .Location in patent: Page/Page column 118
[6]European Journal of Medicinal Chemistry,2012,vol. 53,p. 83 - 97
[7]Patent: WO2013/114332,2013,A1 .Location in patent: Page/Page column 120
[8]Patent: US2014/371204,2014,A1 .Location in patent: Paragraph 0856
[9]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1597 - 1600

4
[ 21304-39-2 ]
[ 333-20-0 ]
[ 79-22-1 ]
[ 35294-61-2 ]

Reference： [1]Patent: DE2129960,1971,
Chem.Abstr.,1972,vol. 76

5
[ 1074-12-0 ]
[ 21304-39-2 ]
[ 119426-64-1 ]
[ 131705-94-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 527 - 532

6
[ 21304-39-2 ]
[ 43002-66-0 ]
1-[2-(4-Chloro-benzyl)-1H-benzoimidazol-5-yl]-ethanone [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 203 - 214

7
[ 21304-39-2 ]
[ 33402-67-4 ]
1-[2-(4-Methoxy-phenyl)-1H-benzoimidazol-5-yl]-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 4h;Reflux;	General procedure: (A)-A mixture of <strong>[21304-39-2]5-acetyl-1,2-diaminobenzene</strong> (d) (10 mmol) and of either sodium hydroxy(R-substituted-phenyl-1-yl)methanesulfonate (f-k) or sodium hydroxy(cyclohexyl or furan-3-yl) methanesulfonate (l-m) (11 mmol) was refluxed for 4 h in 80 mL of ethanol. After cooling, an excess of the sodium salt was filtered off through filter paper and the mother liquors were evaporated to dryness under reduced pressure. The solid residues, coloured from yellow to dark brown, were resuspended in dry ether and then purified, if necessary, by recrystallization from EtOH/H2O, or by silica gel column chromatography, using a mixture of the solvent indicated under the single compounds described below. Compounds 7, 8, 10, 11, 12 have been described previously, as referenced in Fig. 3.

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 215 - 226
[2]European Journal of Medicinal Chemistry,2012,vol. 53,p. 83 - 97

8
[ 21304-39-2 ]
[ 5442-34-2 ]
1-(2-Benzyl-1H-benzoimidazol-5-yl)-ethanone [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 203 - 214

9
[ 21304-39-2 ]
[ 4657-12-9 ]
5-acetyl-2-phenylbenzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 4h;Reflux;	General procedure: (A)-A mixture of <strong>[21304-39-2]5-acetyl-1,2-diaminobenzene</strong> (d) (10 mmol) and of either sodium hydroxy(R-substituted-phenyl-1-yl)methanesulfonate (f-k) or sodium hydroxy(cyclohexyl or furan-3-yl) methanesulfonate (l-m) (11 mmol) was refluxed for 4 h in 80 mL of ethanol. After cooling, an excess of the sodium salt was filtered off through filter paper and the mother liquors were evaporated to dryness under reduced pressure. The solid residues, coloured from yellow to dark brown, were resuspended in dry ether and then purified, if necessary, by recrystallization from EtOH/H2O, or by silica gel column chromatography, using a mixture of the solvent indicated under the single compounds described below. Compounds 7, 8, 10, 11, 12 have been described previously, as referenced in Fig. 3.

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 215 - 226
[2]European Journal of Medicinal Chemistry,2012,vol. 53,p. 83 - 97

10
[ 21304-39-2 ]
[ 58125-69-2 ]
1-[2-(4-Methoxy-benzyl)-1H-benzoimidazol-5-yl]-ethanone [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 203 - 214

11
[ 21304-39-2 ]
[ 141364-38-7 ]
1-[2-(4-Ethoxy-benzyl)-1H-benzoimidazol-5-yl]-ethanone [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 203 - 214

12
[ 21304-39-2 ]
[ 46175-04-6 ]
1-[2-(4-Chloro-phenyl)-1H-benzoimidazol-5-yl]-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 4h;Reflux;	General procedure: (A)-A mixture of <strong>[21304-39-2]5-acetyl-1,2-diaminobenzene</strong> (d) (10 mmol) and of either sodium hydroxy(R-substituted-phenyl-1-yl)methanesulfonate (f-k) or sodium hydroxy(cyclohexyl or furan-3-yl) methanesulfonate (l-m) (11 mmol) was refluxed for 4 h in 80 mL of ethanol. After cooling, an excess of the sodium salt was filtered off through filter paper and the mother liquors were evaporated to dryness under reduced pressure. The solid residues, coloured from yellow to dark brown, were resuspended in dry ether and then purified, if necessary, by recrystallization from EtOH/H2O, or by silica gel column chromatography, using a mixture of the solvent indicated under the single compounds described below. Compounds 7, 8, 10, 11, 12 have been described previously, as referenced in Fig. 3.

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 215 - 226
[2]European Journal of Medicinal Chemistry,2012,vol. 53,p. 83 - 97

13
[ 21304-39-2 ]
sodium (4-ethoxyphenyl)(hydroxy)methanesulfonate [ No CAS ]
1-[2-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-ethanone [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 215 - 226

14
[ 21304-39-2 ]
[ 14527-26-5 ]
[ 79-22-1 ]
[ 31545-28-5 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 574 - 577

15
[ 19602-82-5 ]
[ 21304-39-2 ]
C₂₂H₁₆N₂O₃S₂ [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1994,vol. 96,p. 451 - 452

16
[ 21304-39-2 ]
(5-acetyl-2-ethylamino-phenyl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406

17
[ 21304-39-2 ]
1-[2-(4-amino-furazan-3-yl)-1-ethyl-1H-benzoimidazol-5-yl]-ethanone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3402 - 3406

18
[ 21304-39-2 ]
1-[2-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3H-benzoimidazol-5-yl]-ethanone [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 5807 - 5810
[2]Tetrahedron Letters,2003,vol. 44,p. 5807 - 5810

19
[ 21304-39-2 ]
[ 605674-41-7 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 5807 - 5810
[2]Tetrahedron Letters,2003,vol. 44,p. 5807 - 5810

20
[ 21304-39-2 ]
C₃₀H₂₈N₂O₆ [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 5807 - 5810
[2]Tetrahedron Letters,2003,vol. 44,p. 5807 - 5810

21
[ 21304-39-2 ]
4-Methyl-benzoic acid (2R,3S,5S)-5-[5-acetyl-2-(4-methyl-benzoylamino)-phenylcarbamoyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 5807 - 5810

22
[ 7418-44-2 ]
[ 21304-39-2 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1777 - 1788
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 574 - 577
[3]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1597 - 1600

23
[ 2719-21-3 ]
[ 21304-39-2 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1777 - 1788
[2]Patent: WO2013/114332,2013,A1
[3]Patent: US2014/371204,2014,A1
[4]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1597 - 1600

24
[ 21304-39-2 ]
1-(2-Phenyl-1H-benzoimidazol-5-yl)-ethanol [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 215 - 226

25
[ 21304-39-2 ]
1-(2-Benzyl-1H-benzoimidazol-5-yl)-ethanol [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 203 - 214

26
[ 21304-39-2 ]
1-[2-(4-Chloro-benzyl)-1H-benzoimidazol-5-yl]-ethanol [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 203 - 214

27
[ 21304-39-2 ]
1-[2-(4-Chloro-phenyl)-1H-benzoimidazol-5-yl]-ethanol [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 215 - 226

28
[ 21304-39-2 ]
1-[2-(4-Methoxy-benzyl)-1H-benzoimidazol-5-yl]-ethanol [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 203 - 214

29
[ 21304-39-2 ]
1-(2-(4-methoxyphenyl)-1H-benzimidazol-5-yl)ethanol [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 215 - 226
[2]European Journal of Medicinal Chemistry,2012,vol. 53,p. 83 - 97

30
[ 21304-39-2 ]
1-[2-(4-Ethoxy-benzyl)-1H-benzoimidazol-5-yl]-ethanol [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 203 - 214

31
[ 21304-39-2 ]
1-[2-(4-Ethoxy-phenyl)-1H-benzoimidazol-5-yl]-ethanol [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1988,vol. 43,p. 215 - 226

32
[ 21304-39-2 ]
[ 131706-01-9 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 527 - 532

33
[ 21304-39-2 ]
[ 131706-05-3 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 527 - 532

34
[ 21304-39-2 ]
[ 131706-10-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 527 - 532

35
[ 21304-39-2 ]
[ 131706-06-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 527 - 532

36
[ 21304-39-2 ]
[ 97317-49-2 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 5757,5759

37
[ 21304-39-2 ]
[ 108749-33-3 ]

Reference： [1]Journal of the Chemical Society,1956,p. 2058,2060

38
[ 21304-39-2 ]
5-(N-benzyl-N-methyl-glycyl)-1,3-dihydro-benzimidazol-2-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 5757,5759

39
[ 21304-39-2 ]
[ 65670-90-8 ]

Reference： [1]Patent: DE2720290,1977,
Chem.Abstr.,1978,vol. 88

40
[ 861673-69-0 ]
[ 21304-39-2 ]
1-(3-acetylphenyl)-3-(2-(3-(trifluoromethyl)phenoxy)pyridin-3-yl)thiourea [ No CAS ]
1-(4-acetylphenyl)-3-(2-(3-(trifluoromethyl)phenoxy)pyridin-3-yl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dichloro-ethane; at 20℃;	142b 1- (4-acetylphenyl)-3- (2- (3- (trifluoromethyl) phenoxy) pyridin-3-yl) thiourea (142ba) 1- (3-acetylphenyl)-3- (2- (3- (trifluoromethyl) phenoxy) pyridin-3-yl) thiourea (142bb) [00375] To a suspension of 142a (100 mg, 0.666 mmol) in DCE (4 mL), was slowly added 2- (2-tert-butylphenoxy)-3-isothiocyanatopyridine (94 mg, 0.332 mmol) prepared according to lc. The reaction mixture was stirred at rt over night and concentrated. The crude mixture was used in the next step without further purification.

Reference： [1]Patent: WO2005/70920,2005,A1 .Location in patent: Page/Page column 118-119

41
[ 21304-39-2 ]
[ 146519-40-6 ]

Yield	Reaction Conditions	Operation in experiment
68%		A mixture of <strong>[21304-39-2]1-(3,4-diaminophenyl)ethanone</strong> (Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1985), 24B(5), 574-7., 3.6 g, 24.0 mmol), acetic acid (5 ml, 48.0 mmol) and water (15 ml) was stirred for 10 minutes at 65 C. and the mixture was placed at 5 C. After quenching with water solution of sodium nitrile (1.90 g, 27.6 mmol), the mixture was stirred for 1 hour at 80 C. followed by being cooled to 5 C. with stirring for 3 hours. The formed precipitate was collected and dried to give 1-(1H-1,2,3-benzotriazol-6-yl)ethanone (2.65 g, 68%). 1H NMR (270 MHz, DMSO-d6) delta 2.71 (3H, s), 3.36 (1H, brs), 7.90-8.07 (2H, m), 8.69 (1H, s). MS (ESI) m/z477 (M-H)-, 479 (M+H)+ To a THF (25 ml) solution of 1-(1H-1,2,3-benzotriazol-6-yl)ethanone (1.85 g, 11.5 mmol), (R)-(+)-2-methyl-2-propanesulfinylamide (2.30 g, 18.9 mmol) and titanium(IV) ethoxide (25 ml) were added and the mixture was stirred for 24 hours at 70 C. Then, the mixture was cooled to 0 C. and sodium borohydride (1.5 mg, 40 mmol) was added. After stirring for 2 hours, water and EtOH were added to the mixture with stirring for 1 hour at room temperature. Filtration, evaporation gave N-[(1R)-1-(1H-1,2,3-benzotriazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide (MS (ESI) m/z 265 (M-H)-, 267 (M+H)+) which was treated with hydrochloric acid-MeOH (2.0 M, 15.0 ml) and 1,4-dioxane (15.0 ml) for 1.5 hours at room temperature. Then, the reaction mixture was evaporated and diethyl ether was added to form a precipitate, which was collected, washed with diethyl ether to give (1R)-1-(1H-1,2,3-benzotriazol-5-yl)ethanamine hydrochloride (1.26 g, 68%) MS (ESI) m/z 161 (M-H)- To a DMF (10 ml) solution of (1R)-1-(1H-1,2,3-benzotriazol-5-yl)ethanamine hydrochloride (500 mg, 2.52 mmol) and the compound of Example 3A (614 mg, 2.52 mmol), HBTU (1.24 g, 3.28 mmol) and trimethylamine (1.1 ml, 7.56 mmol) were added and the mixture was stirred for 2 hours at room temperature. The reaction was quenched with water and the product was extracted with EtOAc. Then, evaporation, purification through HPLC (column: MS C 30×50 mm, solvent: acetonitrile/0.01% aqueous ammonia eluting with 4 to 40) gave the title compound (120 mg, 12%) as a white solid. The fraction time for the desired product was 5.7 minutes. 1H NMR (300 MHz, DMSO-d6) delta 1.38 (3H, s), 1.47 (3H, d, H, J=6.6 Hz), 4.57 (2H, s), 5.12-5.22 (1H, m), 6.62 (2H, d, J=11.7 Hz), 7.41 (1H, d, J=8.1 Mz), 7.80 (1H, s), 7.85 (1H, d, J=8.8 Hz), 8.66 (1H, d, J=8.1 Mz). MS (ESI) m/z 387 (M-H)-, 389 (M+H)+
68%		A mixture of <strong>[21304-39-2]1-(3,4-diaminophenyl)ethanone</strong> (Indian Journal of Chemistry, Section B: OrganicChemistry Including Medicinal Chemistry (1985), 24B(5), 574-7., 3.6 g, 24.0 mmol), acetic acid (5 ml, 48.0 mmol) and water (15 ml) was stirred for 10 minutes at 65 0C and the mixture was placed at 5 0C. After quenching with water solution of sodium nitrile (1.90 g, 27.6 mmol), the mixture was stirred for 1hour at 800C followed by being cooled to 5 0C with stirring for 3 hours. The formed precipitate was collected and dried to give 2.65 g (68 %) of the title compound. 1H NMR (270 MHz, DMSO-d6) delta ppm 2.71 (3H, s), 3.36(1 H, brs), 7.90-8.07 (2H, m), 8.69 (1 H, s). MS (ESI) m/z 477 (M - H)", 479 (M + H)+.

Reference： [1]Patent: US2006/270682,2006,A1 .Location in patent: Page/Page column 29
[2]Patent: WO2008/7211,2008,A1 .Location in patent: Page/Page column 38

42
[ 506-68-3 ]
[ 21304-39-2 ]
[ 1432-42-4 ]
[ 67469-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroquinone;palladium; In methanol; water; ethyl acetate;	(a) 5-Acetyl-2-aminobenzimidazole (for Example 9) 4-Amino-3-nitroacetophenone (38.7 g.) in ethyl acetate (1 l.) containing hydroquinone (10 mg.) was hydrogenated over 10% palladium-on-charcoal at room temperature and atmospheric pressure, until hydrogen uptake ceased. The catalyst was removed by filtration and the filtrate was evaporated. The solid product was stirred in water (100 ml.), separated and dried to give <strong>[21304-39-2]3,4-diaminoacetophenone</strong> (28.6 g.) m.p. 131-4 C. Cyanogen bromide (20 g.) in water (400 ml.) was added to a stirred suspension of <strong>[21304-39-2]3,4-diaminoacetophenone</strong> (25 g.) in methanol (400 ml.). The solution was kept at room temperature for 16 hours and then evaporated. The residue was dissolved in water and the solution was basified with an excess of saturated sodium carbonate solution. The suspension obtained was stirred for 1 hour, filtered, washed with water and dried to give 5-acetyl-2-aminobenzimidazole (26.6 g.), m.p. 228-234 C.

Reference： [1]Patent: US4167569,1979,A

43
vanadyl acetate [ No CAS ]
C₉H₁₉COC₈H₁₇CCHO^(1-)*Na⁽¹⁺⁾=C₉H₁₉COC₈H₁₇CCHONa [ No CAS ]
[ 21304-39-2 ]
sodium [1,2-di(2'-octyl-3'-oxo-1'-dodecenylamino)-4-(3''-oxo-1''-propionyl)benzeno]vanadyl(II) [ No CAS ]
[1,2-di(2'-octyl-3'-oxo-1'-dodecenylamino)-4-acetylbenzeno]vanadyl(II) [ No CAS ]

Reference： [1]Inorganic Chemistry,2000,vol. 39,p. 4879 - 4885

44
C₉H₁₉COC₈H₁₇CCHO^(1-)*Na⁽¹⁺⁾=C₉H₁₉COC₈H₁₇CCHONa [ No CAS ]
[ 21304-39-2 ]
[ 373-02-4 ]
[1,2-di(2'-octyl-3'-oxo-1'-dodecenylamino)-4-acetylbenzeno]nickel(II) [ No CAS ]

Reference： [1]Inorganic Chemistry,2000,vol. 39,p. 4879 - 4885

45
C₉H₁₉COC₈H₁₇CCHO^(1-)*Na⁽¹⁺⁾=C₉H₁₉COC₈H₁₇CCHONa [ No CAS ]
[ 21304-39-2 ]
[ 142-71-2 ]
[1,2-di(2'-octyl-3'-oxo-1'-dodecenylamino)-4-acetylbenzeno]copper(II) [ No CAS ]

Reference： [1]Inorganic Chemistry,2000,vol. 39,p. 4879 - 4885

46
sodium; (2,4-dimethoxy-phenyl)-hydroxy-methanesulfonate [ No CAS ]
[ 21304-39-2 ]
[ 1224878-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 4h;Reflux;	General procedure: (A)-A mixture of <strong>[21304-39-2]5-acetyl-1,2-diaminobenzene</strong> (d) (10 mmol) and of either sodium hydroxy(R-substituted-phenyl-1-yl)methanesulfonate (f-k) or sodium hydroxy(cyclohexyl or furan-3-yl) methanesulfonate (l-m) (11 mmol) was refluxed for 4 h in 80 mL of ethanol. After cooling, an excess of the sodium salt was filtered off through filter paper and the mother liquors were evaporated to dryness under reduced pressure. The solid residues, coloured from yellow to dark brown, were resuspended in dry ether and then purified, if necessary, by recrystallization from EtOH/H2O, or by silica gel column chromatography, using a mixture of the solvent indicated under the single compounds described below. Compounds 7, 8, 10, 11, 12 have been described previously, as referenced in Fig. 3.

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2937 - 2953
[2]European Journal of Medicinal Chemistry,2012,vol. 53,p. 83 - 97

47
[ 949490-29-3 ]
[ 21304-39-2 ]
[ 1224878-10-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 4h;Reflux;	General procedure: (A)-A mixture of <strong>[21304-39-2]5-acetyl-1,2-diaminobenzene</strong> (d) (10 mmol) and of either sodium hydroxy(R-substituted-phenyl-1-yl)methanesulfonate (f-k) or sodium hydroxy(cyclohexyl or furan-3-yl) methanesulfonate (l-m) (11 mmol) was refluxed for 4 h in 80 mL of ethanol. After cooling, an excess of the sodium salt was filtered off through filter paper and the mother liquors were evaporated to dryness under reduced pressure. The solid residues, coloured from yellow to dark brown, were resuspended in dry ether and then purified, if necessary, by recrystallization from EtOH/H2O, or by silica gel column chromatography, using a mixture of the solvent indicated under the single compounds described below. Compounds 7, 8, 10, 11, 12 have been described previously, as referenced in Fig. 3.

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2937 - 2953
[2]European Journal of Medicinal Chemistry,2012,vol. 53,p. 83 - 97

48
C₉H₁₉COC₈H₁₇CCHO^(1-)*Na⁽¹⁺⁾=C₉H₁₉COC₈H₁₇CCHONa [ No CAS ]
[ 21304-39-2 ]
sodium [1,2-di(2'-octyl-3'-oxo-1'-dodecenylamino)-4-(3''-oxo-1''-propionyl)benzeno]copper(II) [ No CAS ]

Reference： [1]Inorganic Chemistry,2000,vol. 39,p. 4879 - 4885

49
[ 1238855-02-1 ]
[ 21304-39-2 ]
[ 1238855-18-9 ]

Reference： [1]Medicinal Chemistry,2010,vol. 6,p. 70 - 78

50
[ 21304-39-2 ]
[ 1238855-26-9 ]

Reference： [1]Medicinal Chemistry,2010,vol. 6,p. 70 - 78

51
[ 21304-39-2 ]
[ 1238855-36-1 ]

Reference： [1]Medicinal Chemistry,2010,vol. 6,p. 70 - 78

52
[ 152782-75-7 ]
[ 21304-39-2 ]
[ 1383484-93-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	In ethanol; for 4h;Reflux;	General procedure: (A)-A mixture of <strong>[21304-39-2]5-acetyl-1,2-diaminobenzene</strong> (d) (10 mmol) and of either sodium hydroxy(R-substituted-phenyl-1-yl)methanesulfonate (f-k) or sodium hydroxy(cyclohexyl or furan-3-yl) methanesulfonate (l-m) (11 mmol) was refluxed for 4 h in 80 mL of ethanol. After cooling, an excess of the sodium salt was filtered off through filter paper and the mother liquors were evaporated to dryness under reduced pressure. The solid residues, coloured from yellow to dark brown, were resuspended in dry ether and then purified, if necessary, by recrystallization from EtOH/H2O, or by silica gel column chromatography, using a mixture of the solvent indicated under the single compounds described below. Compounds 7, 8, 10, 11, 12 have been described previously, as referenced in Fig. 3.