Water → 2-Aminocarbonylamino-4-chloro-5-(2-naphthyl)pyrrole-3-carboxamide

HRID 416030Notes

Reaction equation

HRID 416030 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].[Cl:23]N1C(=O)CCC1=O.O>CN(C)C=O>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[C:8]([Cl:23])[C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 461809882-Aminocarbonylamino-5-(2-naphthyl)pyrrole-3-carboxamide

Product 1

HCID 582940372-Aminocarbonylamino-4-chloro-5-(2-naphthyl)pyrrole-3-carboxamideYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-aminocarbonylamino-5-(2-naphthyl)pyrrole-3-carboxamide (Compound No. 1-1, 92 mg, 0.31 mmol) and N-chlorosuccinimide (46 mg, 0.34 mmol) in anhydrous N,N-dimethylformamide (2 mL) was stirred at 60° C. for 2 hours. After cooling, water (10 mL) was added thereto, the precipitated solid was filtered off, and washed with water (10 mL) and acetone (10 mL). The obtained solid was dried at 50° C. under reduced pressure to give the target compound (46 mg) as a pale brown solid (Yield 45%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid was filtered off
  3. washwashed with water (10 mL) and acetone (10 mL)
  4. customThe obtained solid was dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-1cf96be556f44b5ba843c18e3f773bd9
Source dataset
uspto-grants-2012_01
Patent number
US08088817B2

Reaction notes

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