Acetic Acid → [(3-Indolyl)(4-methylphenylsulfonyl)]methane

HRID 2412820Notes

Reaction equation

HRID 2412820 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]1([CH3:19])[CH:15]=[CH:14][C:13]([S:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.[Na+].[C:21](O)(=O)C.CN(C)C=O>ClC1C=CC=CC=1.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:12]2[CH:11]=[C:10]([CH3:19])[CH:15]=[CH:14][C:13]=2[S:16]([CH3:21])(=[O:18])=[O:17])=[CH:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 798IndoleHCID 6228DimethylformamideHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 20431077[(3-Indolyl)(4-methylphenylsulfonyl)]methane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 5.0 g (0.043 mole) of indole, 1.5 g (0.05 mole) of p-formaldehyde, 7.65 g (0.043 mole) of sodium p-toluenesulfinate, 3.87 ml of glacial acetic acid and 36.6 ml of N,N-dimethylformamide was heated at approximately 150° C. for approximately four hours. The slightly cooled reaction mixture was then slowly poured with stirring into approximately 110 ml of water and 75.0 ml of chlorobenzene was added. The layers were separated after approximately twenty minutes and the water layer extracted a second time with 75.0 ml of fresh chlorobenzene and separated. The organic extracts were combined, washed with cold water and separated. A solid separated and was collected by filtration from the combined chlorobenzene layers and dried to obtain 2.18 g of [(3-indolyl)(4-methylphenylsulfonyl)]methane (Formula X: R=4--CH3 ; R1 =R2 =R3 =R4 =H; n=0) as a white solid which melted at 152°-153° C. developing a dark purple color.

Workup

  1. customThe slightly cooled reaction mixture
  2. additionwas then slowly poured
  3. additionwas added
  4. customThe layers were separated after approximately twenty minutes
  5. extractionthe water layer extracted a second time with 75.0 ml of fresh chlorobenzene
  6. customseparated
  7. washwashed with cold water
  8. customseparated
  9. customA solid separated
  10. filtrationwas collected by filtration from the combined chlorobenzene layers
  11. customdried

Sources & evidence

ORD record
ord-6d468f944f5143f3a3d742e55c736261
Source dataset
uspto-grants-1985_01
Patent number
US04494989

Reaction notes

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