4-Toluenesulfonyl chloride → HCID 13720817, compound

HRID 330187Notes

Reaction equation

HRID 330187 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].CCCCCC>CC(=O)CC>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chloride2×HCID 8058HexaneHCID 11430Potassium Carbonate2×HCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 13720817HCID 13720817, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of methyl indole-5-carboxylate, (21.7 g), p-toluenesulfonyl chloride (47.3 g), and K2CO3 (68.4 g) in 2-butanone (310 ml) was refluxed under a nitrogen atmosphere for 18 hr. Additional p-toluenesulfonyl chloride (12.0 g) and K2CO3 (17 g) was added to the reaction mixture and reflux was continued for 18 hr. The reaction mixture was filtered hot and the filtrate was evaporated to give an ivory solid that was tritrated with hexane to give methyl 1-(4-methylphenylsulfonyl)indole-5-carboxylate (23.0 g, 56%) as an ivory solid: NMR (80 MHz, CDCl3): 2.34 (s, 3H, ArCH3), 3.91 (s, 3H, OCH3), 6.7 (d, 1H, H2 -indole).

Workup

  1. temperaturereflux
  2. filtrationThe reaction mixture was filtered hot
  3. customthe filtrate was evaporated
  4. customto give an ivory solid that

Sources & evidence

ORD record
ord-476cdd2dfd9b4c228ea3ee8f46551288
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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