Acetic Acid → HCID 23444955, compound

HRID 397883Notes

Reaction equation

HRID 397883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][CH3:21])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:22](O)(=[O:24])C>C=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([CH2:22][OH:24])=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][CH3:21])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 69039758HCID 69039758, compound

Product 1

HCID 23444955HCID 23444955, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of {1-[1-(3,4-dichloro-phenyl)-1H-imidazol-4-ylmethyl]-1H-imidazol-2-yl}-methyl-amine (0.60 g, 1.7 mmol) in acetic acid (7 ml) and aqueous formaldehyde (2 ml of a 37% solution) was stirred at 20° C. for 96 h. The reaction mixture was evaporated to dryness and chromatographed [silica, elution with gradient CH2Cl2 to 50% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)] to obtain the free base of the title compound. It was crystallized as the off-white hydrochloride salt (0.030 g, 5%). Mp.>180° C. dec. (MeOH/Et2O), MS: m/e=352 (M+H+).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customchromatographed
  3. wash[silica, elution with gradient CH2Cl2 to 50% (CH2Cl2/MeOH/aq. NH4OH=90:10:1)]

Sources & evidence

ORD record
ord-975850e739994c1e91af5bd094dae9ee
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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