2-(4-((2-Butyl-4-chloro-5-formylimidazol-1-yl)methyl)phenyl)benzonitrile → HCID 178441683, compound

HRID 375456Notes

Reaction equation

HRID 375456 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]#[N:27])=[CH:16][CH:15]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].C([Sn]([N:53]=[N+:54]=[N-:55])(CCCCCCCC)CCCCCCCC)CCCCCCC>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:55][N:54]=[N:53][N:27]=3)=[CH:18][CH:19]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 233522922-(4-((2-Butyl-4-chloro-5-formylimidazol-1-yl)methyl)phenyl)benzonitrileHCID 713541223-(Trioctylstannyl)triaza-1,2-dien-2-ium-1-ide

Product 1

HCID 178441683HCID 178441683, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2.11 g of 2-butyl-4-chloro-5-formyl-1-(2'-cyanobiphenyl-4-yl)methylimidazole, 8.38 g of trioctyltin azide (tri-n-octyltin azide) and 10 ml of toluene was stirred at 120° C. for 18 hours. After cooling, the reaction mixture was concentrated. To the residue was added 10 ml of ethanol as well as an aqueous solution of sodium nitrite (1.3 g/5 ml) and the mixture was adjusted to pH 3.3 with concentrated hydrochloric acid. The mixture was diluted with 20 ml of water and extracted with two 20 ml portions of ethyl acetate. The ethyl acetate solution was concentrated and the residue was purified by chromatography on 30 g of silica gel (CH2Cl2 -MeOH). The active fraction was concentrated to provide 1.82 g of 2-butyl-4-chloro-5-formyl-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylimidazole. Yield 73%. 1H NMR (CDCl3) δ: 0.78-1.80 (9H), 2.53 (3H, t), 5.51 (2H, s), 6.9-8.0 (12H, m), 9.66 (1H, s) IR(KBr): 2964, 1668, 1518, 1466, 1382, 1280, 758 cm-1

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. additionTo the residue was added 10 ml of ethanol as well as an aqueous solution of sodium nitrite (1.3 g/5 ml)
  4. additionThe mixture was diluted with 20 ml of water
  5. extractionextracted with two 20 ml portions of ethyl acetate
  6. concentrationThe ethyl acetate solution was concentrated
  7. customthe residue was purified by chromatography on 30 g of silica gel (CH2Cl2 -MeOH)
  8. concentrationThe active fraction was concentrated

Sources & evidence

ORD record
ord-3ffff3cbc9bd43189f0ed0d609dd0053
Source dataset
uspto-grants-1996_01
Patent number
US05484955

Reaction notes

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