Ammonium Hydroxide → 2-(5-Nitro-3-sulfamoyl-indol-1-yl)-acetamide

HRID 23407Notes

Reaction equation

HRID 23407 reaction equation
[C:1]([CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[C:7]([S:17](Cl)(=[O:19])=[O:18])=[CH:6]1)(=[O:3])[NH2:2].[OH-].[NH4+:22]>C(Cl)Cl>[N+:14]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][C:1]([NH2:2])=[O:3])[CH:6]=[C:7]2[S:17](=[O:19])(=[O:18])[NH2:22])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 225739891-carbamoylmethyl-5-nitro-1H-indole-3-sulfonyl chloride

Product 1

HCID 225740602-(5-Nitro-3-sulfamoyl-indol-1-yl)-acetamideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 1-carbamoylmethyl-5-nitro-1H-indole-3-sulfonyl chloride (0.37 g, 1.165 mmole) of Step 2 was suspended in methylene chloride (2 ml) and added to ammonium hydroxide (4 ml) at room temperature. After stirring for 2 h at room temperature, the reaction flask was heated on a steam bath for 35 min and then allowed to cool to room temperature. The yellow solid which precipitated was filtered off and dried to afford 0.24 g (0.81 mmole, 69% yield) of 2-(5-nitro-3-sulfamoyl-indol-1-yl)-acetamide. Step 4

Workup

  1. temperaturethe reaction flask was heated on a steam bath for 35 min
  2. temperatureto cool to room temperature
  3. customThe yellow solid which precipitated
  4. filtrationwas filtered off
  5. customdried

Sources & evidence

ORD record
ord-cc37e04e2103426789e12188b678ff98
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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