Hydrochloric Acid → HCID 14539878, compound

HRID 962757Notes

Reaction equation

HRID 962757 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].S(Cl)([Cl:15])=O.[Cl-].[Al+3].[Cl-].[Cl-].[C:21]1([S:27]([N:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31]2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>ClC(Cl)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:30]([S:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:29])=[O:28])[CH:31]=2)=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8468Vanillic AcidHCID 24386Thionyl ChlorideHCID 3150171-(Phenylsulfonyl)-1H-indoleHCID 6451240Aluminum(III) Chloride

Product 2

HCID 14539878HCID 14539878, compoundHCID 19085532HCID 19085532, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent3×

Procedure

4-Hydroxy-3-methoxybenzoyl chloride, which was prepared from 4-hydroxy-3-methoxybenzoic acid (1.01 g) and thionyl chloride (0.53 ml), was dissolved in dichloroethane (10 ml). The resultant solution was added on ice to a suspension of aluminum chloride (2.08 g) in dichloroethane (20 ml). Following, 1-(phenylsulfonyl)indole (1.85 g) in dichloroethane (10 ml) was added to the resultant with cooling on ice bath and stirred for 1.5 hours at room temperature. The reaction mixture was poured into 1N HCl (100 ml). The precipitate was collected by filtration and washed with water and methanol, obtaining 1.22 g of 3-(4-hydroxy-3-methoxybenzoyl)-1-(phenylsulfonyl)-indole as colorless crystals.

Workup

  1. temperaturewith cooling on ice bath
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water and methanol

Sources & evidence

ORD record
ord-82d171cb89cd49ff99aef2a631babc2b
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Reaction notes

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