Toluene → HCID 20184834, compound

HRID 2309858Notes

Reaction equation

HRID 2309858 reaction equation
C1([CH:7](C2C=CC(N(C)C)=CC=2)[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:17])[C:9]=2[C:18]([OH:20])=[O:19])C=CC=CC=1.[C:30]1(C)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:11]1([C:14]2[C:15]([C:33]3[CH:32]=[CH:31][C:30]([N:10]([CH3:17])[CH3:9])=[CH:35][CH:34]=3)=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]([CH3:17])[C:9]([C:18]([OH:20])=[O:19])=[C:8]3[CH3:7])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 13561338HCID 13561338, compound

Product 1

HCID 20184834HCID 20184834, compound

Conditions

Temperature
40 °C

Procedure

With stirring a mixture of 325.0 ml of ethanol, 47.5 g of [(phenyl)(4-dimethylaminophenyl)(4-methylphenylsulfonyl)]methane, 25.0 ml of 1-methylindol-2-carboxylic acid and 13.0 ml of concentrated hydrochloric acid was heated at reflux temperature for approximately twenty-two hours. The resultant solution was poured slowly into approximately 300.0 ml of cold water. The resulting suspension was extracted with approximately 500.0 ml of toluene. The toluene layer was separated and washed consecutively with water and saturated sodium chloride solution. The toluene layer was stirred for approximately one hour with decolorizing charcoal and filtered to remove the charcoal. The toluene was removed by evaporation leaving a dark blue-purple solid. The solid was suspended in ethanol, heated for approximately one hour and cooled to ambient temperature. The solid was collected by filtration, washed with isopropanol and dried to obtain 19.0 g of a mixture of starting methane and [(phenyl)(4-dimethylaminophenyl)(1-methyl-2-carboxyindol-3-yl]methane as determined by nuclear magnetic resonance spectroscopy. The resulting solid was suspended in approximately 300.0 ml of toluene for approximately one hour and the solid collected by filtration. The toluene-wet solid was reslurried in approximately 100.0 ml of toluene at a temperature of approximately 60° C. for approximately one hour. After cooling the slurry to approximately 40° C., the solid was collected by filtration and dried to obtain 2.47 g of [(phenyl)(4-dimethylaminophenyl)(1-methyl-2-carboxyindol-3-yl)]methane (Formula XI: R1 =R2 =R3 =R4 =R11 =B"=H; R5 =N(CH3)2 ; R9 =CH3), a cream-colored solid which melted at 214°-215° C. A significant infrared maximum appeared at 760 (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 acidic clay-coated paper slowly developed a medium blue-colored image and spotted on a phenolic resin-coated paper slowly developed a dark blue-colored image.

Workup

  1. filtrationthe solid collected by filtration
  2. filtrationthe solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-d7308bea2d7f43dbbecbab0bde5c22ca
Source dataset
uspto-grants-1987_09
Patent number
US04697018

Reaction notes

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