Potassium Cyanide → HCID 86761106, compound

HRID 2235569Notes

Reaction equation

HRID 2235569 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14]1[N:18]([CH3:19])[C:17]2[C:20]([N:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]=1.[C-:31]#[N:32].[K+]>CS(C)=O.O>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]([NH:13][C:14]2[N:18]([CH3:19])[C:17]3[C:20]([N:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])=[CH:21][CH:22]=[CH:23][C:16]=3[N:15]=2)=[C:6]([CH:11]=1)[O:5][CH:4]([CH2:3][CH3:2])[C:31]#[N:32]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 58896487HCID 58896487, compound

Product 1

HCID 86761106HCID 86761106, compoundYield 106.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 80 mg (0.16 mmol) of N2-[2-(3-bromopropoxy)-4-chlorophenyl]-1-methyl-N7,N7-dipropyl-1H-benzimidazole-2,7-diamine in 2 mL of dimethylsulfoxide was added 13 mg (0.19 mmol) of potassium cyanide. The reaction was stirred at room temperature for several hours, diluted with 10 mL water, and extracted twice with 10 mL ethyl acetate. The organics were washed with water, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography eluting with a solution of 20% acetone/hexanes to give 75 mg (100%) of the title compound.

Workup

  1. extractionextracted twice with 10 mL ethyl acetate
  2. washThe organics were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography
  7. washeluting with a solution of 20% acetone/hexanes

Sources & evidence

ORD record
ord-302c814f6637427586b5c0b697862e21
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

Loading…