HCID 21180499, compound → HCID 9861789, compound

HRID 1386931Notes

Reaction equation

HRID 1386931 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[C:17]#[N:18])=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH2:17][NH2:18])=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 21180499HCID 21180499, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9861789HCID 9861789, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[2-(3,4-dichloro-phenyl)-3H-imidazol-4-yl]-benzonitrile (4.1 g, 13 mmol), in THF (130 ml) was slowly added to an ice-cooled mixture of lithium aluminum hydride (0.99 g, 26 mmol) in THF (130 ml). The mixture was stirred for 30 min. at r.t., then saturated Seignette-salt solution (5 ml) was added slowly and stirring was continued for 30 min. The precipitate was filtered and the organic phase evaporated and chromatographed over SiO2 with CH2Cl2—CH3OH—NH4OH (140:10:1) to obtain 3-[2-(3,4-dichloro-phenyl)-3H-imidazol-4-yl]-benzylamine (1.77 g, 43%) as a foam. The hydrochloride salt was then prepared which was crystallized to an off-white solid. Mp. >250° C. (MeOH/Et2O), MS: m/e=318 (M+H+).

Workup

  1. temperaturecooled
  2. stirringstirring
  3. waitwas continued for 30 min
  4. filtrationThe precipitate was filtered
  5. customthe organic phase evaporated
  6. customchromatographed over SiO2 with CH2Cl2—CH3OH—NH4OH (140:10:1)

Sources & evidence

ORD record
ord-897d5a7b1d7f4f069b08c4b6f6e812de
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

Loading…