反应 #215058

反应方程式

1-ethyl-2-methylindole

hydrochloric acid

sodium p-toluenesulfinate

p-dimethylaminobenzaldehyde

triethanolamine

→

[(4-dimethylaminophenyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane

收率 83.6%

溶剂

ethyl alcohol

反应条件

后处理

1. 1
   workup.STIRRINGafter stirring approximately twenty minutes at room temperature
2. 2
   温度the temperature was raised to and
3. 3
   温度maintained at 55°-60° C. for approximately twenty minutes
4. 4
   温度After cooling to approximately 10° C.
5. 5
   过滤the separated pink solid was collected by filtration
6. 6
   洗涤washed with 100.0 ml of cold ethyl alcohol
7. 7
   workup.ADDITIONThe solid was then suspended in a mixture of 350.0 ml of water and 10.0 g of triethanolamine at ambient temperature for approximately thirty minutes
8. 8
   过滤collected by filtration
9. 9
   洗涤washed first with 150.0 ml of 3 percent aqueous triethanolamine and finally with 150.0 ml of water
10. 10
    其他After drying in vacuo at 40° C.

实验过程

To a stirred mixture of 175.0 ml of ethyl alcohol, 27.5 ml of concentrated hydrochloric acid, 30.4 g (0.15 mole) of 86.4 percent sodium p-toluenesulfinate and 18.5 g (0.125 mole) of p-dimethylaminobenzaldehyde chilled to approximately 5° C., there was slowly added 19.5 g (0.113 mole) of 91.2 percent 1-ethyl-2-methylindole. The resulting mixture was stirred for approximately three and one half hours at ambient temperature, during which period the color changed from blue to yellow. The pH of the mixture was adjusted to approximately 8 by the addition of 40.0 g of triethanolamine and, after stirring approximately twenty minutes at room temperature, the temperature was raised to and maintained at 55°-60° C. for approximately twenty minutes. After cooling to approximately 10° C., the separated pink solid was collected by filtration and washed with 100.0 ml of cold ethyl alcohol. The solid was then suspended in a mixture of 350.0 ml of water and 10.0 g of triethanolamine at ambient temperature for approximately thirty minutes, collected by filtration and washed first with 150.0 ml of 3 percent aqueous triethanolamine and finally with 150.0 ml of water. After drying in vacuo at 40° C., there was obtained 42.2 g of [(4-dimethylaminophenyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane (Formula II: R=4--CH3 ; R1 =C2H5 ; R2 =CH3 ; R3 =R5 =H; R6 =N(CH3)2) which softened at 155° C. and melted at 159°-161° C.

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