Hydrochloric Acid → [(4-Dimethylaminophenyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane

HRID 127876

반응식

HRID 127876 반응식
Cl.[C:2]1([CH3:11])[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18](C=O)=[CH:17][CH:16]=1.[CH2:24]([N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1[CH3:35])[CH3:25].N(CCO)(CCO)[CH2:37]CO>C(O)C>[CH3:23][N:14]([CH3:13])[C:15]1[CH:16]=[CH:17][C:18]([C:3]2[C:4]([C:28]3[C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:26]([CH2:24][CH3:25])[C:27]=3[CH3:35])=[C:5]([S:8]([CH3:37])(=[O:10])=[O:9])[CH:6]=[CH:7][C:2]=2[CH3:11])=[CH:21][CH:22]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 7618TriethanolamineHCID 1704321H-Indole, 1-ethyl-2-methyl-HCID 2723791Sodium p-toluenesulfinate

생성물 1

HCID 20184815[(4-Dimethylaminophenyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane수율 83.6%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
5 °C

실험 절차

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.

후처리

  1. stirringafter stirring approximately twenty minutes at room temperature
  2. temperaturethe temperature was raised to and
  3. temperaturemaintained at 55°-60° C. for approximately twenty minutes
  4. temperatureAfter cooling to approximately 10° C.
  5. filtrationthe separated pink solid was collected by filtration
  6. washwashed with 100.0 ml of cold ethyl alcohol
  7. 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. filtrationcollected by filtration
  9. washwashed first with 150.0 ml of 3 percent aqueous triethanolamine and finally with 150.0 ml of water
  10. customAfter drying in vacuo at 40° C.

출처 및 근거

ORD 기록
ord-9a2b5827be304d20af8d3e648a221494
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04257954

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