Water → 1-methyl-5-nitro-1H-indole-3-sulfonyl chloride

HRID 583923Notes

Reaction equation

HRID 583923 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=2)[CH:16]=[CH:15]1.O>ClCCl>[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=2)[C:16]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 24638Chlorosulfonic acidHCID 1473221H-Indole, 1-methyl-5-nitro-

Product 1

HCID 223447291-methyl-5-nitro-1H-indole-3-sulfonyl chlorideYield 10.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chlorosulfonic acid (1.9 mL, 28 mmol) and Na2SO4 (403 mg, 2.8 mmol) in dichloromethane (17 mL) was treated with a solution of 1-methyl-5-nitro-1H-indole (500 mg, 2.8 mmol) in dichloromethane (11 mL) over 1 hour, stirred for 30 minutes, and decanted to provide a thick brown oil. The oil was slowly treated with water (20 mL), stirred for 10 minutes, and filtered. The filtrate was dried in a vacuum oven to provide 80 mg of the desired compound which was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-7ac62a324a9144d280d77893c41fa36b
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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