Acetone → [Bis(4-dimethylaminophenyl)(2-methylindol-3-yl)]methane

HRID 637863

Reaction equation

HRID 637863 reaction equation
[OH-].[K+].[CH3:3][N:4]([CH3:31])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:22]3[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)=[C:13](S(C)(=O)=O)[CH:14]=[CH:15][C:16]=2[CH3:17])=[CH:7][CH:6]=1.[CH3:32][C:33]1[NH:34]C2C(C=1)=CC=CC=2.[CH3:42]C(C)=O>O.C(O)(C)C>[CH3:29][N:28]([CH3:30])[C:25]1[CH:26]=[CH:27][C:22]([C:12]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([N:4]([CH3:3])[CH3:31])=[CH:6][CH:7]=3)=[C:16]3[C:15](=[CH:14][CH:13]=2)[NH:34][C:33]([CH3:32])=[C:17]3[CH3:42])=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 72242-MethylindoleHCID 14797Potassium HydroxideHCID 20184810[Bis(4-dimethylaminophenyl)(4-methylphenylsulfonyl)]methane

Product 1

HCID 20184812[Bis(4-dimethylaminophenyl)(2-methylindol-3-yl)]methane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Two grams of potassium hydroxide was added slowly to a mixture of 6.3 g of [bis(4-dimethylaminophenyl)(4-methylphenylsulfonyl)]methane, 2.5 g of 2-methylindole and 75.0 ml of acetone. The resulting slurry was stirred for approximately 24 hours at ambient temperature. Fifty milliliters of isopropyl alcohol was added to the reaction mixture to effect complete solution. Slowly with stirring, the resulting solution was added to one liter of water and the solid which formed was collected by filtration. The wet filter cake was suspended in 100.0 ml of isopropyl alcohol and stirred approximately thirty minutes. The solid was collected by filtration, washed twice with 25.0 ml of isopropyl alcohol each and dried to obtain 5.1 g of [bis(4-dimethylaminophenyl)(2-methylindol-3-yl)]methane (Formula IV: R1 =R2 =R4 =R9 =R11 =H; R3 =R5 =N(CH3)2 ; R10 =CH3), a pale gray-colored solid which melted at 198°-202° C. A significant infrared maximum appeared at 740 (C--H;s) cm-1. The nuclear magnetic resonance spectrum was concordant with the assigned structure. A toluene solution of the product spotted on an acid clay-coated paper or a phenolic resin-coated paper slowly developed a grape-colored image.

Workup

  1. stirringSlowly with stirring
  2. customthe solid which formed
  3. filtrationwas collected by filtration
  4. stirringstirred approximately thirty minutes
  5. filtrationThe solid was collected by filtration
  6. washwashed twice with 25.0 ml of isopropyl alcohol each and
  7. customdried

Sources & evidence

ORD record
ord-972f759569bd4d7381a40d3ab6b88287
Source dataset
uspto-grants-1985_12
Patent number
US04558137

Linked notes

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