Water → HCID 178509441, compound

HRID 460877Notes

Reaction equation

HRID 460877 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([C:21]#[N:22])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([C:23]#[N:24])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:27][C:28]([F:37])([F:36])[C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32].O>CS(C)=O>[C:23]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:20]1[CH:19]=[CH:18][C:17]([C:21](=[NH:22])[NH:32][C:31]3[CH:33]=[CH:34][CH:35]=[C:29]([C:28]([F:36])([F:37])[F:27])[CH:30]=3)=[CH:16][C:15]2=1)#[N:24]

Participants

6

Reactant 4

HCID 962WaterHCID 73753-(Trifluoromethyl)anilineHCID 24758Sodium hydrideHCID 213948759-Benzyl-9H-carbazole-3,6-dicarbonitrile

Product 1

HCID 178509441HCID 178509441, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A slurry of 9-benzyl-3,6-dicyanocarbazole (3.8 g, see Example 3C) and sodium hydride (50% in oil, 1.21 g) in 20 ml of dimethylsulfoxide is treated dropwise with m-trifluoromethylaniline (4.04 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 1.5 g of 6-cyano-9-(phenylmethyl)-N-[3-(trifluoromethyl)phenyl]- 3-carbazolecarboximidamide. Elution with 20% ethyl acetate/dichloromethane/methanol (2:7:1) yields 2g of the desired diamidine, which is recrystallized from two liters of water containing 10 ml of concentrated hydrochloric acid to yield 1.6 g of the title compound, melting point 210°-220° 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-1f6717f1e20a45a88bc8f88155aac577
Source dataset
uspto-grants-1977_12
Patent number
US04061655

Reaction notes

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