Water → 5-Nitroindole-1-carboxilic acid phenylamide

HRID 2376907Notes

Reaction equation

HRID 2376907 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)([O-:5])=[O:4].[C:15]1([N:21]=[C:22]=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[C:15]1([NH:21][C:22]([N:11]2[C:12]3[C:8](=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:14][CH:13]=3)[CH:9]=[CH:10]2)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 225235-NitroindoleHCID 24758Sodium hydride

Product 1

HCID 210548545-Nitroindole-1-carboxilic acid phenylamideYield 1,000%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (802 mg, 20.0 mmol, 60% in oil) was suspended in N,N-dimethylformamide (40 ml); 5-nitroindole (2.50 g, 15.4 mmol) was added thereto; and the reaction mixture was stirred at room temperature for 30 minutes. Phenyl isocyanate (2.01 ml, 1.23 mmol) was added thereto, and the reaction mixture was stirred at room temperature for 1.5 hours. Water (80 ml) was added to the reaction mixture; the reaction mixture was stirred at room temperature for 30 minutes; and the precipitated crystals were filtered off, washed by water and diethyl ether one by one, and dried by means F of suction to yield the title compound (3.53 g, 12.3 mmol, 79.8%) as pale yellow crystals.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1.5 hours
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. filtrationand the precipitated crystals were filtered off
  4. washwashed by water and diethyl ether one by one
  5. customdried by means F of suction

Sources & evidence

ORD record
ord-7ec54da851df432ea4bf313ce6818348
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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