ChemicalBook CAS DataBase List 4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile

4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile synthesis

13synthesis methods

Product Name:4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile
CAS Number:114772-55-3
Molecular formula:C22H22ClN3O
Molecular Weight:379.88

83857-96-9 Synthesis

83857-96-9
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114772-54-2
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4’-[(2-butyl-4-chloro-5-hydroxymethyl)-1H-imidazol-1-yl)methyl]-[1,1’-Biphenyl]-2-carbonitrile

114772-55-3
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Yield:114772-55-3 88%

Reaction Conditions:

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 1.5 h;

Steps:

1
Example-1 [117] [118] Preparation of 2-n-Butyl-4-chloro-l-[2'-(cyanobiphenyl-4-yl) methyl] -5-(hydroxymethyl)-imidazole (IV); [119] A mixture of 4'-Bromomethyl-2-cyanobiphenyl(II) (125.0 g), l-Methyl-2-pyrrolidinone (NMP) (375.0 ml), anhydrous potassium carbonate (76.0 g) and 2-Butyl-4-chloro-5-formylimidazole (III) (90.0 g) was heated at 7O⁰C to 75⁰C for about 4-5 hrs. Sodium borohydride (18.0 g) was charged to the reaction mixture at 3O⁰C. Water (1875.0 ml) was added to it and isopropanol (562.5 ml) was added to the wet cake and heated at 75-8O⁰C for 1.5 hours. The reaction mixture was cooled at room temperature and filtered. The solid was suck dried and dried in oven to give the title compound (153.0g).[120] Yield: 88.0%[121] Purity (By HPLC): 99.1%

References:

ALEMBIC LIMITED;DEO, Keshav;DESAI, Sanjay;RATHOD, Dhiraj;PARIKH, Chirag;MOKAL, Ramesh WO2010/29457, 2010, A2 Location in patent:Page/Page column 11-12

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124750-67-0 Synthesis