Water → HCID 178448417, compound

HRID 460875Notes

Reaction equation

HRID 460875 reaction equation
[CH2:1]([N:5]1[C:17]2[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:20]#[N:21])[CH:10]=2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[F:24][C:25]([F:34])([F:33])[C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29].O>CS(C)=O>[CH2:1]([N:5]1[C:17]2[CH:16]=[CH:15][C:14]([C:18](=[NH:19])[NH:29][C:28]3[CH:30]=[CH:31][CH:32]=[C:26]([C:25]([F:33])([F:34])[F:24])[CH:27]=3)=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:20]#[N:21])[CH:10]=2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 73753-(Trifluoromethyl)anilineHCID 24758Sodium hydrideHCID 21394878HCID 21394878, compound

Product 1

HCID 178448417HCID 178448417, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A slurry of 9-butyl-3,6-dicyanocarbazole (4 g, see Example 1C) and sodium hydride (50% in oil, 1.41 g) in 20 ml of anhydrous dimethylsulfoxide is treated dropwise with m-trifluoromethylaniline (4.72 g). The reaction mixture is stirred at room temperature for four days and then poured into 500 ml of water and stirred vigorously for two hours. The resultant precipitate is collected by filtration and purified by column chromatography using one liter of silica gel. Elution with dichloromethane and 1% ethyl acetate/dichloromethane yields 1.8 g of 9-butyl-6-cyano-N-[3-(trifluoromethyl)-phenyl]-9H-carbazole-3-carboximidamide. Elution with 20% ethyl acetate/dichloromethane and ethyl acetate/dichloromethane/methanol (2:7:1) yields 1.6 g of the desired diamidine, which is recrystallized from two liters of water containing 15 ml of 10% hydrochloric acid to yield 1.5 g of the title compound, melting point 205°-210° C.

Workup

  1. stirringstirred vigorously for two hours
  2. filtrationThe resultant precipitate is collected by filtration
  3. custompurified by column chromatography
  4. washElution with dichloromethane and 1% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-48c2d6a6dcd14004ba8e80580989257f
Source dataset
uspto-grants-1977_12
Patent number
US04061655

Reaction notes

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