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114772-55-3

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Basic Information
CAS No.: 114772-55-3
Name: 4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile
Article Data: 250
Molecular Structure:
Molecular Structure of 114772-55-3 (4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile)
Formula: C22H22ClN3O
Molecular Weight: 379.889
Synonyms: 2-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]-5-hydroxymethylimidazole;4'-(2-Butyl-4-chloro-5-hydroxymethyl-1H-imidazol-1-yl)-1,1'-biphenyl-2-carbonitrile;
Density: 1.191 g/cm3
Boiling Point: 605.615 °C at 760 mmHg
Flash Point: 320.065 °C
Appearance: white
PSA: 61.84000
LogP: 4.95838
Related products
Synthetic route
124750-67-0

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]imidazole-5-carboxaldehyde

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate In toluene at 25 - 45℃; for 4h; Product distribution / selectivity;100%
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;83.7%
With sodium tetrahydroborate In methanol at -12 - -10℃; Inert atmosphere; Large scale;71.2%
83857-96-9

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde

114772-54-2

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
Stage #1: 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde; 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile With potassium carbonate In 1-methyl-pyrrolidin-2-one at 70 - 75℃;
Stage #2: With sodium tetrahydroborate In 1-methyl-pyrrolidin-2-one at 30℃;
Stage #3: With water In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 75 - 80℃; for 1.5h;		88%
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃;
With tetrabutylammomium bromide; water; sodium hydroxide In toluene at 20℃;

potassium (2-cyanophenyl)trifluoroborate

151012-31-6

2-n-Butyl-4-chloro-1-(4-bromobenzyl)-1H-imidazole-5-methanol

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water for 18h; Product distribution / selectivity; Heating / reflux;84%
With N-ethyl-N,N-diisopropylamine; palladium diacetate; triphenylphosphine In ethanol; water for 18h; Product distribution / selectivity; Heating / reflux;
Stage #1: triisopropyl phosphite; triphenylphosphine; palladium dichloride In tetrahydrofuran at 25℃;
Stage #2: potassium (2-cyanophenyl)trifluoroborate; 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-1H-imidazole-5-methanol With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethanol; water at 25℃; for 18h; Product distribution / selectivity; Heating / reflux;
Stage #1: palladium diacetate; tris-(o-tolyl)phosphine In tetrahydrofuran at 25 - 60℃; for 0.5h;
Stage #2: potassium (2-cyanophenyl)trifluoroborate; 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-1H-imidazole-5-methanol With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethanol; water at 25℃; for 18h; Product distribution / selectivity; Heating / reflux;
79047-41-9

2-n-butyl-4-chloro-5-hydroxymethylimidazole

114772-54-2

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
Stage #1: 2-n-butyl-4-chloro-5-hydroxymethylimidazole With sodium methylate In N,N-dimethyl-formamide at 25℃; for 0.5h;
Stage #2: 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile In N,N-dimethyl-formamide at 20℃; for 24h;		40%
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;
57246-71-6

methyl pentanimidate

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaOH / H2O; methanol; toluene
1.2: 55 percent / POCl3 / toluene / 2 h / 100 °C
2.1: 90 percent / NaBH4 / methanol / 2 h / 20 °C
3.1: NaOMe / dimethylformamide / 0.5 h / 25 °C
3.2: 40 percent / dimethylformamide / 24 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: sodium methylate / methanol / 2 h / 0 °C / Green chemistry
2: trichlorophosphate / toluene / 2 h / 60 - 100 °C / Green chemistry
3: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C / Green chemistry
4: sodium tetrahydroborate / methanol / 1.17 h / 20 - 40 °C / Green chemistry
View Scheme
83857-96-9

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 90 percent / NaBH4 / methanol / 2 h / 20 °C
2.1: NaOMe / dimethylformamide / 0.5 h / 25 °C
2.2: 40 percent / dimethylformamide / 24 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C / Green chemistry
2: sodium tetrahydroborate / methanol / 1.17 h / 20 - 40 °C / Green chemistry
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 12 h / -10 °C / Inert atmosphere
2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl acetamide / 5 h / 20 °C
2: sodium tetrahydroborate / methanol; N,N-dimethyl acetamide / 1 h / 5 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate; tetraethylammonium bromide / toluene / 90 - 95 °C
2: sodium tetrahydroborate; sodium hydroxide / water / 20 - 85 °C
View Scheme
57598-33-1

2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran / 2 h / 20 °C
2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
3: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
4: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
View Scheme
114772-53-1

2-Cyano-4'-methylbiphenyl

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
2: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
View Scheme
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile) / dichloromethane / 24 h / 40 - 42 °C / Reflux; Large scale
2: potassium carbonate / N,N-dimethyl acetamide / 4 h / -12 - -8 °C / Inert atmosphere; Large scale
3: sodium tetrahydroborate / methanol / -12 - -10 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 3 steps
1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 80 °C / Green chemistry
2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C / Green chemistry
3: sodium tetrahydroborate / methanol / 1.17 h / 20 - 40 °C / Green chemistry
View Scheme
74201-13-1

N-(2-hydroxy-1,1-dimethyl)-2-methoxybenzamide

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: thionyl chloride / 1 h / 25 °C
2: tetrahydrofuran / 2 h / 20 °C
3: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
4: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
View Scheme
84392-32-5

4,4-dimethyl-2-(4'-methyl-biphenyl-2-yl)-4,5-dihydrooxazole

114772-55-3

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
View Scheme
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Specification

The 4'-[(2-Butyl-4-chloro-5-hydroxymethyl-1H-imidazol-1-yl)methyl]-1,1'-biphenyl-2-carbonitrile with its cas register number is 114772-55-3. It also can be called as  4'-[[2-Butyl-4-chloro-5-(hydroxymethyl)-1H-imidazol-1-yl]methyl]-[1,1'-biphenyl]-2-carbonitrile and the Systematic name about this chemical is 4'-{[2-butyl-4-chloro-5-(hydroxymethyl)-1H-imidazol-1-yl]methyl}biphenyl-2-carbonitrile. It belongs to the Losartan Potassium.

Physical properties about 4'-[(2-Butyl-4-chloro-5-hydroxymethyl-1H-imidazol-1-yl)methyl]-1,1'-biphenyl-2-carbonitrile are: (1)ACD/LogP: 4.00; (2)ACD/LogD (pH 5.5): 4; (3)ACD/LogD (pH 7.4): 4; (4)ACD/BCF (pH 5.5): 324; (5)ACD/BCF (pH 7.4): 347; (6)ACD/KOC (pH 5.5): 2136; (7)ACD/KOC (pH 7.4): 2291; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 8; (11)Polar Surface Area: 61.84Å2; (12)Index of Refraction: 1.609; (13)Molar Refractivity: 110.483 cm3; (14)Molar Volume: 319.084 cm3; (15)Polarizability: 43.799x10-24cm3; (16)Surface Tension: 45.217 dyne/cm; (17)Enthalpy of Vaporization: 94.672 kJ/mol

You can still convert the following datas into molecular structure:
(1)SMILES: CCCCc3nc(Cl)c(CO)n3Cc1ccc(cc1)c2ccccc2C#N
(2)InChI: InChI=1/C22H22ClN3O/c1-2-3-8-21-25-22(23)20(15-27)26(21)14-16-9-11-17(12-10-16)19-7-5-4-6-18(19)13-24/h4-7,9-12,27H,2-3,8,14-15H2,1H3
(3)InChIKey: FGCNIDUBRIVYBP-UHFFFAOYAX
(4)Std. InChI: InChI=1S/C22H22ClN3O/c1-2-3-8-21-25-22(23)20(15-27)26(21)14-16-9-11-17(12-10-16)19-7-5-4-6-18(19)13-24/h4-7,9-12,27H,2-3,8,14-15H2,1H3
(5)Std. InChIKey: FGCNIDUBRIVYBP-UHFFFAOYSA-N