79047-41-9

Usage

Chemical Properties

White Crystalline Solid

Uses

2-Butyl-5-chloroimidazole-4-methanol (Losartan EP Impurity A) is an impurity of Losartan.

InChI:InChI=1/C8H13ClN2O/c1-2-3-4-7-10-6(5-12)8(9)11-7/h12H,2-5H2,1H3,(H,10,11)

Synthetic route

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 2h;	90%
With hydrogen; magnesium In methanol at 20℃; under 258.574 - 413.718 Torr; for 0.583333h;

5-benzyloxymethyl-2-butyl-4-chloro-1H-imidazole (679412-76-1) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
With methanesulfonic acid In chloroform at 20℃; for 1h;	90%

2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + 2-butyl-4,5-dichloroimidazole

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran	A 65% B 10%

1,4-dioxane (123-91-1) + 2-n-butyl-4,5-di-(hydroxymethyl)-1H-imidazole (136317-69-6) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
With N-chloro-succinimide In ethanol	51%

sodium dichloroisocyanurate dihydrate + 2-n-butyl-4,5-di-(hydroxymethyl)-1H-imidazole (136317-69-6) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
In 1,4-dioxane; ethanol	50%

2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
With N-chloro-succinimide
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran; acetonitrile / 2 h / 0 °C 2: 1.) NCS, 2.) Zn, AcOH / 1.) THF, acetonitrile, from -5 deg C to 0 deg C, 0.75 h, 2.) frp, -5 deg C to 0 deg C, 1.5 h View Scheme
With N-chloro-succinimide In water; ethyl acetate

2-Butyl-5-trimethylsilanyloxymethyl-1H-imidazole (153258-24-3) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + 2-Butyl-4,5-dichloro-4-trimethylsilanyloxymethyl-4H-imidazole

Conditions	Yield
With N-chloro-succinimide; acetic acid; zinc 1.) THF, acetonitrile, from -5 deg C to 0 deg C, 0.75 h, 2.) frp, -5 deg C to 0 deg C, 1.5 h; Yield given. Multistep reaction. Title compound not separated from byproducts;

N-(2-benzyloxy-1-cyanoethyl)pentanamide (679412-75-0) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / CCl4; PPh3 / acetonitrile / 4 h / 45 °C 2: 90 percent / methanesulfonic acid / CHCl3 / 1 h / 20 °C View Scheme

methyl pentanimidate (57246-71-6) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
Multi-step reaction with 2 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 View Scheme

ethyl 2-butyl-1H-imidazole-4(5)carboxylate (148990-06-1) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / DIBAL / toluene 2: NCS View Scheme

ethyl methyl ether (540-67-0) + 2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran; diethyl ether	16 g (52%)

sode de l'acide trichloroisocyanurique (2893-78-9) + 2-n-butyl-4,5-di-(hydroxymethyl)-1H-imidazole (136317-69-6) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
In 1,4-dioxane; ethanol

N-chloro-succinimide (128-09-6) + 2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) → 2-butyl-4,5-10 dichloroimidazole + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
In tetrahydrofuran; 2-methoxy-ethanol; water

2-methoxy-ethanol (109-86-4) + 2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) → 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9)

Conditions	Yield
With N-chloro-succinimide In 1,4-dioxane; water; ethyl acetate

(NH4)2 Ce(NO3)6 + dichloromethane (75-09-2) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With potassium hydroxide In water; acetic acid	92%
In water; acetic acid

4-hydroxy[1]benzopyran-2-one (1076-38-6) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + malononitrile (109-77-3) → 2-amino-4-(2-butyl-4-chloro-1H-imidazol-5-yl)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile

Conditions	Yield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 9h;	81%

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-butyl-4-chloro-5-[(t-butyldimethylsilyloxy)methyl]imidazole (137582-52-6)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 3.5h; Ambient temperature;	80%

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole (133051-88-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;	80%

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + β-naphthol (135-19-3) + malononitrile (109-77-3) → 2-amino-4-(2-butyl-4-chloro-1H-imidazol-5-yl)-4H-benzo[g]chromene-3-carbonitrile

Conditions	Yield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 12h;	79%

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With ammonium cerium(IV) nitrate In acetic acid at 25℃; for 3h;	77%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; iodine; sodium hydrogencarbonate In water; toluene at 20℃; for 16h;	690 mg
With oxygen; Pt/Bi on graphite In methanol at 60℃; under 2250.23 Torr; for 6h; Product distribution; Further Variations:; Reagents;
With manganese dioxide In dichloromethane	12.81 g (86%)

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + malononitrile (109-77-3) + recorcinol (108-46-3) → 2-amino-4-(2-butyl-4-chloro-1H-imidazol-5-yl)-7-hydroxy-4H-chromene-3-carbonitrile

Conditions	Yield
With dimethyl sulfoxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 14h;	74%

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole (114772-55-3)

Conditions	Yield
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;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + methyl 4'-(bromomethyl)-3'-fluorobiphenyl-2-carboxylate (138459-24-2) → methyl 3'-fluoro-4'-<<2-butyl-4-chloro-5-(hydroxymethyl)-1H-imidazol-1-yl>methyl>biphenyl-2-carboxylate (138459-25-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;	30%

methanol (67-56-1) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-butyl-4-chloro-1H-imidazole-5-carboxylic acid,methyl ester (124750-71-6)

Conditions	Yield
With manganese(IV) oxide; sodium cyanide; acetic acid 1.) THF; Multistep reaction;

1,4-bis(bromomethyl)benzene (623-24-5) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → [1-(4-Bromomethyl-benzyl)-2-butyl-5-chloro-1H-imidazol-4-yl]-methanol + [3-(4-Bromomethyl-benzyl)-2-butyl-5-chloro-3H-imidazol-4-yl]-methanol

Conditions	Yield
With sodium methylate 1.) methanol, 0 deg C, 2.) DMF, 25 deg C; Multistep reaction;

6-bromomethyl-2-naphthalenecarbonitrile (56358-46-4) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 6-(2-Butyl-5-chloro-4-hydroxymethyl-imidazol-1-ylmethyl)-naphthalene-2-carbonitrile (135943-07-6) + 2-n-butyl-4-chloro-5-(hydroxymethyl)-1-<(2-cyanonaphthalen-6-yl)methyl>imidazole (135943-02-1)

Conditions	Yield
With sodium hydride 1.) DMF, 25 deg C, 1 h, 2.) DMF, RT, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

4-(bromomethyl)benzaldehyde (51359-78-5) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 4-(2-Butyl-5-chloro-4-hydroxymethyl-imidazol-1-ylmethyl)-benzaldehyde (125665-59-0) + 1-(4-formylbenzyl)-2-butyl-4-chloro-5-hydroxymethylimidazole (114773-11-4)

Conditions	Yield
With sodium methylate 1.) methanol, 0 deg C, 2.) DMF, 25 deg C; Multistep reaction;

methyl 4'-(bromomethyl)-[1,1'-biphenyl]-3-carboxylate (114772-37-1) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-butyl-1-<(3'-carbomethoxybiphenyl-4-yl)methyl>-4-chloro-5-(hydroxymethyl)imidazole (114772-41-7)

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) 40 deg C, 4 h; Yield given. Multistep reaction;

methyl 2-[4-(bromomethyl)benzoyl]benzoate (114772-96-2) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-butyl-1-<4-(2-carbomethoxybenzoyl)benzyl>-4-chloro-5-(hydroxymethyl)imidazole (114772-97-3)

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) 40 deg C, 4 h; Yield given. Multistep reaction;

methyl 2-[4-(bromomethyl)phenoxy]benzoate (30087-38-8) + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-butyl-4-chloro-1-[4-(2-carbomethoxyphenoxy)benzyl]-5-hydroxymethylimidazole (114772-89-3)

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) 40 deg C, 4 h; Multistep reaction;

2-(4-Bromomethyl-phenylsulfanyl)-benzoic acid methyl ester + 2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-[4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-ylmethyl)-phenylsulfanyl]-benzoic acid methyl ester

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) 40 deg C, 4 h; Multistep reaction;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + methyl 4-(bromomethyl)-3-fluorobenzoate (128577-47-9) → 4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-ylmethyl)-3-fluoro-benzoic acid methyl ester (138459-26-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + 4'-bromomethyl-2-nitrobiphenyl (114772-39-3) → 2-butyl-4-chloro-5-(hydroxymethyl)-1-<(2'-nitrobiphenyl-4-yl)methyl>imidazole (124750-43-2)

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + Methyl 4'-(bromomethyl)biphenyl-2-carboxylate (114772-38-2) → 2-butyl-4-chloro-5-hydroxymethyl-1-[(2'-methoxycarbonyl-1,1'-biphenyl-4-yl)methyl]-1H-imidazole (114772-43-9)

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Yield given. Multistep reaction;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + 2-(4-Bromomethyl-phenyl)-furan-3-carboxylic acid ethyl ester → 2-[4-(2-Butyl-4-chloro-5-hydroxymethyl-imidazol-1-ylmethyl)-phenyl]-furan-3-carboxylic acid ethyl ester

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + methyl 4'-methyl-2',6'-dimethoxy<1,1'-biphenyl>-2-carboxylate (134360-53-5) → 4'-<<2-butyl-4-chloro-5-(hydroxymethyl)-1H-imidazolyl>methyl>-2',6'-dimethoxy<1,1'-biphenyl>-2-carboxylic acid methyl ester (134360-55-7) + 4'-<<2-butyl-4-(hydroxymethyl)-5-chloro-1H-imidazolyl>methyl>-2',6'-dimethoxy<1,1'-biphenyl>-2-carboxylic acid methyl ester (134360-56-8)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + 5-(4'-Bromomethyl-biphenyl-2-yl)-3H-[1,2,3]triazole-4-carbonitrile → 2-butyl-4-chloro-1-<<2'-(5-cyano-1,2,3-triazol-4-yl)biphenyl-4-yl>methyl>-5-(hydroxymethyl)imidazole (125573-80-0)

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole (133051-88-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) + {2-Butyl-5-chloro-1-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazol-4-yl}-methanol

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Product distribution; Ambient temperature; various ratios of reagents;
With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + 3-(4'-Bromomethyl-biphenyl-2-yl)-5-trifluoromethyl-4-trityl-4H-[1,2,4]triazole → {2-Butyl-5-chloro-3-[2'-(5-trifluoromethyl-4-trityl-4H-[1,2,4]triazol-3-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-yl}-methanol

Conditions	Yield
With sodium methylate 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h; Multistep reaction;

Upstream product

• 153258-24-3 2-Butyl-5-trimethylsilanyloxymethyl-1H-imidazole 
• 109-86-4 2-methoxy-ethanol 
• 68283-19-2 2-butyl-5-hydroxymethyl-1H-imidazole 
• 679412-76-1 2-butyl-4-chloro-5-benzyloxymethyl-1H-imidazole 
• 128-09-6 N-chloro-succinimide 
• 136317-69-6 2-n-butyl-4,5-di-(hydroxymethyl)-1H-imidazole 
• 2893-78-9 sode de l'acide trichloroisocyanurique 
• 123-91-1 1,4-dioxane 
• 540-67-0 ethyl methyl ether 
• 148990-06-1 ethyl 2-butyl-1H-imidazole-4⁽⁵⁾carboxylate 
• 57246-71-6 methyl pentanimidate 
• 679412-75-0 N-(2-benzyloxy-1-cyanoethyl)pentanamide 
• 679412-76-1 5-benzyloxymethyl-2-butyl-4-chloro-1H-imidazole 
• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 

Downstream Products

• 125685-33-8 2-n-butyl-5-chloro-1-<(3-cyanophenyl)methyl>-4-(hydroxymethyl)imidazole 
• 125665-57-8 2-n-butyl-4-chloro-1-<(3-cyanophenyl)methyl>-5-(hydroxymethyl)imidazole 
• 114799-93-8 2-n-butyl-5-chloro-4-(hydroxymethyl)-1-<(4-nitrophenyl)methyl>imidazole 
• 114799-92-7 2-Butyl-4-chloro-1-[(4-nitrophenyl)methyl]-1H-imidazole-5-methanol 
• 151012-31-6 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-1H-imidazole-5-methanol 
• 133909-99-6 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol 
• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 
• 137997-24-1 1-[(3-Ethoxycarbonyl-2-phenylimidazo[1,2-a]pyridin-6-yl)methyl]-2-butyl-4-chloro-5-formylimidazole 
• 114798-89-9 (S)-2-[4-(2-Butyl-4-chloro-5-methoxymethyl-imidazol-1-ylmethyl)-benzoylamino]-3-phenyl-propionic acid 
• 125665-54-5 (R)-2-[4-(2-Butyl-4-chloro-5-methoxymethyl-imidazol-1-ylmethyl)-benzoylamino]-3-phenyl-propionic acid 
• 114822-93-4 (S)-1-[4-(2-Butyl-4-chloro-5-methoxymethyl-imidazol-1-ylmethyl)-benzoyl]-pyrrolidine-2-carboxylic acid 
• 125665-55-6 (R)-1-[4-(2-Butyl-4-chloro-5-methoxymethyl-imidazol-1-ylmethyl)-benzoyl]-pyrrolidine-2-carboxylic acid 
• 114772-10-0 1-(4-Aminobenzyl)-2-n-butyl-4-chloro-5-(methoxymethyl)imidazole 
• 124749-75-3 methyl 2-n-butyl-4-chloro-1-<<4-amino>phenyl>methyl>imidazole-5-acetate 

Relevant academic research and scientific papers

Reduction of aldehydes and oximes to their corresponding alcohols and amines by catalytic hydrogenation method

The reduction of aldehydes such as 2-butyl-5-chloro-3H-imidazole-5- carbaldehyde and veratraldehyde, which are pharmaceutical key intermediates, have been reduced to alcohols by catalytic hydrogenation method in the presence of magnesium and also oximes are reduced to primary amines successively by magnesium/ammonium formate system, is a large scale feasible and cheaper method. The crystal structure of the product, (2-butyl-5-chloro-3H-imidazole-4-yl)- methanol 1 is reported.

New method for the synthesis of diversely functionalized imidazoles from N-acylated α-aminonitriles

(Equation presented) A new general method for the synthesis of medicinally important diversely functionalized imidazoles from N-acylated α-aminonitriles has been developed. N-Acylated α-aminonitriles were reacted with triphenylphosphine and carbon tetrahalide to afford 2,4-disubstituted 5-halo-1H-imidazoles in good yield. This new methodology was applied for the synthesis of 2-butyl-4-chloro-5-hydroxymethylimidazole. These halo-imidazoles can be directly converted to 2,4,5-trisubstituted imidazoles through palladium-catalyzed coupling reactions.

Process for preparing 2,4,5-trisubstituted imidazoles from N-acylated alpha-amino nitriles

The invention is a process for preparing an imidazole of formula I which comprises treating an N-acylated α-amino nitrile with a phosphine and a carbon tetrahalide of the formula CX4, wherein X is Cl or Br, to form a haloimidazole of the formula wherein R1 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2-aryl, and aryl; and R2 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2—O-aryl and aryl; and X is selected from the group consisting of Cl and Br.

Crystal structures of two imidazole derivatives

2-n-Butyl-5-chloro-3H-imidazole-4-carbaldehyde (BCIC), C8H 11ClN2O. F.W.= 186.64, monoclinic, P21/c, a=7.2617(3)A, b= 13.2067(6)A, c=9.8491(4)A β = 101.76(1)°, V= 924.74(7)A3, Z=4, Dcal = 1.341 Mgm-3, μ = 0.367mm-1, F000=392, λ (MoKα) = 0.71073A, final R1 and wR2 are 0.049 and 0.126, respectively. 2-n-Butyl-4-chloro-1 [(2-cyanobiphenyl-4-yl)methyl]-5- hydroxymethyl imidazok (BCCI), CvfliufilNnO, F.W. = 379.88, triclinic, P 1 a = 8.198(2)A, b = 10.997(3)A, c = 11.524(2)A, α= 90.83(2)°, β= 94.31(2)°, γ = 109.45(2)°, V= 976.0(2)A3, Z=2, Dcal = 1.293Mgm-3, μ = 1.856mm-1, F000 = 400, λ (CuKα) = 1.5418A, final R1 and wR2 are 0.081 and 0.239, respectively. The imidazole ring in both the molecules is planar. The n-butyl group adopts a bent conformation in BCIC where it is in extended conformation in BCCI. The biphenyl ring system orients at an angle of 45.1(1)° in BCCI. The molecules are stabilized by N-H...N and O-H... N type hydrogen bonds in addition to van der Waals forces.

Substituted imidazolyl-alkylthio-alkanoic acids

Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.

Process for synthesizing 4-halo-5-(hydroxymethyl) imidazole compounds

A process for preparing, on an industrial scale, 4-halo-5-(hydroxymethyl) imidazole compounds that are useful as intermediates for medicines. A 4-chloro-5-(hydroxymethyl) imidazole compound, a 4-bromo-5-(hydroxymethyl) imidazole compound or a like compound is synthesized by reacting a 4,5-bis(hydroxymethyl) imidazole compound with a halogenating agent such as an N-chlorosuccinimide, an N-bromosuccinimide, a chlorinated isocyanuric acid compound or the like compound.

N-(heteroaryl) imidazolyl-alkenoic acids having angiotension II receptor antagonist activity

Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.

Method for purification of 2-alkyl-4-halo-5-formylimidazoles

The invention provides a method of purifying 2-alkyl-4-halo-5-formylimidazoles, which comprises dissolving an 2-alkyl-4-halo-5-formylimidazole in an aqueous solution of a sulfonating agent, adjusting the solution to pH 1-6, and removing the impurity 2-alkyl-4,5-dihaloimidazole by filtration or extraction.

QUINOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION, AND THEIR THERAPEUTIC APPLICATIONS

The present invention provides a compound which is a quinoline derivative of the formula (I) STR1 in which R 1 represents either 1H-tetrazol-5-yl, or CO 2 H,R 2 represents either (C 1-7) alkyl or (C 2-6)alkenyl,R 3 and R 4 represent, independently of each other, hydrogen, halogen, cyano group, (C 1-7) alkyl, (C 3-7)cycloalkyl(C 1-4)alkyl, aryl, aryl(C 1-4)alkyl, aryl(C 2-6)alkenyl,--(CH 2) m--COR 5 in which m=0 to 4 and R 5 represents hydrogen,--OH,--(C. sub.1-6)alkoxy, or--NR 7 R. sub.8, R 7 and R 8 representing, independently of each other, hydrogen or--(C 1-4)alkyl group, or a--(CH 2) n--R 6 group in which n=1 to 4 and R 6 represents--OH,--(C 1-6)alkoxy,--(C 1-4) alkoxy--(C 1-4) alkoxy, or (C. sub.3-7)cycloalkyl(C 1-4)alkoxy group, or a pharmaceutically acceptable salt thereof and their therapeutic applications.

A practical synthesis of 2-butyl-4(5)-chloro-5(4)-hydroxymethyl-1H-imidazole

A practical process for the synthesis of 2-butyl-4-hydroxymethyl imidazole (4) followed by chlorination to provide chloroimidazole 1 in an overall 71% yield has been developed.