Acetaldehyde → [(Methyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane

HRID 127877

Reaction equation

HRID 127877 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7]([O-:9])=[O:8])=[CH:3][CH:2]=1.[Na+].[CH2:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH3:23])[CH3:13].[CH:24](=O)[CH3:25].Cl.[CH2:28](O)C>>[CH3:1][C:2]1[C:3]([C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]([CH2:12][CH3:13])[C:15]=2[CH3:23])=[C:4]([S:7]([CH3:28])(=[O:9])=[O:8])[CH:5]=[CH:6][C:24]=1[CH3:25]

Participants

6

Reactant 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 702EthanolHCID 1704321H-Indole, 1-ethyl-2-methyl-HCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 20431076[(Methyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane

Conditions

Temperature
5 °C

Procedure

To a stirred mixture of 175.0 ml of ethyl alcohol, 30.35 g (0.14 mole) of 81.4 percent sodium p-toluenesulfinate, 19.5 g (0.112 mole) of 91.2 percent 1-ethyl-2-methylindole and 5.5 g (0.125 mole) of acetaldehyde under an atmosphere of nitrogen and maintaining the temperature at approximately 5° C. by means of an ice-water bath, there was added dropwise 27.5 ml of concentrated hydrochloric acid. After stirring approximately four hours at ambient temperature, the white solid which had separated was collected by filtration, washed with a small amount of ethyl alcohol and air dried to a constant weight of 43.7 g. The solid was dissolved in a hot mixture of ethyl and methyl alcohols, treated with 3.0 g of decolorizing charcoal, the solution filtered while hot, and then set aside at ambient temperature overnight. The resulting slurry was placed in a refrigerator for approximately two hours. The separated solid was then collected by filtration, washed with 500.0 ml of ethyl alcohol and air-dried to obtain 17.8 g of [(methyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane (Formula X: R=4--CH3 ; R1 =C2H5 ; R2 =CH3 ; R3 =R4 =H; n=1), a pale yellow solid which melted at 140°-142° C. developing a purple color.

Workup

  1. customthe white solid which had separated
  2. filtrationwas collected by filtration
  3. washwashed with a small amount of ethyl alcohol and air
  4. customdried to a constant weight of 43.7 g
  5. dissolutionThe solid was dissolved in a hot mixture of ethyl and methyl alcohols
  6. additiontreated with 3.0 g of decolorizing charcoal
  7. filtrationthe solution filtered while hot, and
  8. waitthen set aside at ambient temperature overnight
  9. waitThe resulting slurry was placed in a refrigerator for approximately two hours
  10. filtrationThe separated solid was then collected by filtration
  11. washwashed with 500.0 ml of ethyl alcohol
  12. customair-dried

Sources & evidence

ORD record
ord-755d69c262524ec3989f6f32ad2463c2
Source dataset
uspto-grants-1981_03
Patent number
US04257954

Linked notes

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