Water → 2-[3-(2-Cyanopyrrol-1-yl)benzoyl]guanidine

HRID 399877Notes

Reaction equation

HRID 399877 reaction equation
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].[C:9]([C:11]1[N:12]([C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=2)[C:19](OC)=[O:20])[CH:13]=[CH:14][CH:15]=1)#[N:10].O>CN(C)C=O>[C:9]([C:11]1[N:12]([C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=2)[C:19]([N:7]=[C:6]([NH2:8])[NH2:5])=[O:20])[CH:13]=[CH:14][CH:15]=1)#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 18945318Methyl 3-(2-cyanopyrrol-1-yl)benzoate

Product 1

HCID 189451892-[3-(2-Cyanopyrrol-1-yl)benzoyl]guanidineYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28% Methanolic sodium methoxide (122.2 ml) was added to a solution of guanidine hydrochloride (63.7 g) in dry N,N-dimethylformamide (300 ml) and the mixture was stirred for 20 minutes at ambient temperature. To the mixture was added methyl 3-(2-cyanopyrrol-1-yl)benzoate (30.5 g), and the mixture was stirred for 2 hours at the same temperature. The reaction mixture was poured into water under stirring. The isolated precipitate was collected by filtration to give 2-[3-(2-cyanopyrrol-1-yl)benzoyl]guanidine (21.66 g).

Workup

  1. stirringthe mixture was stirred for 2 hours at the same temperature
  2. stirringunder stirring
  3. filtrationThe isolated precipitate was collected by filtration

Sources & evidence

ORD record
ord-7103577844754c4eb7e2a352b01c9ad8
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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