Water → HCID 14736086, compound

HRID 583922Notes

Reaction equation

HRID 583922 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[O-]S([O-])(=O)=O.[Na+].[Na+].[N+:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2)([O-:15])=[O:14].O>ClCCl>[N+:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[S:2]([Cl:1])(=[O:5])=[O:3])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 225235-NitroindoleHCID 24436Sodium SulfateHCID 24638Chlorosulfonic acid

Product 1

HCID 14736086HCID 14736086, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chlorosulfonic acid (3 mL, 45 mmol) and Na2SO4 (700 mg, 4.9 mmol) in dichloromethane (30 mL) was treated dropwise with a solution of 5-nitroindole (800 mg, 4.9 mmol) in dichloromethane (20 mL) over 1 hour, stirred for another 30 minures, and decanted to provide a thick brown oil. The oil was slowly treated with water (20 mL), stirred for 10 minutes, filtered, and dried in a vacuum oven to provide 651 mg of the desired product.

Workup

  1. customdecanted
  2. customto provide a thick brown oil
  3. stirringstirred for 10 minutes
  4. filtrationfiltered
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-16fa9d8f96544e009da4a6cbc0246cae
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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