5-Chloro-N1-Methylbenzene-1,2-diaMine → HCID 67154999, compound

HRID 1897615Notes

Reaction equation

HRID 1897615 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1.[CH2:11]([O:13][CH:14]([O:23][CH2:24][CH3:25])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[CH:21]=O)[CH3:12]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[C:21]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:15]=3[CH:14]([O:23][CH2:24][CH3:25])[O:13][CH2:11][CH3:12])[N:8]([CH3:9])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 121982665-Chloro-N1-Methylbenzene-1,2-diaMineHCID 85772009HCID 85772009, compound

Product 1

HCID 67154999HCID 67154999, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-chloro-N1-methylbenzene-1,2-diamine (383 mg, 2.446 mmol) and 4-diethoxymethyl-pyridine-3-carbaldehyde (512 mg, 2.446 mmol) in 1,4-dioxane (20 mL) was heated to 75° C. overnight. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel flash chromatography employing heptane-ethyl acetate (1:1) to give of 6-chloro-2-(4-diethoxymethyl-pyridin-3-yl)-1-methyl-1H-benzoimidazole.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c853e4d7ff9742d0b204013206845da2
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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