Water → HCID 18945428, compound

HRID 399868Notes

Reaction equation

HRID 399868 reaction equation
[ClH:1].[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].[OH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)[CH:20]=1)[C:14](OC)=[O:15].O>CN(C)C=O.CO>[ClH:1].[OH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([N:21]2[CH:22]=[CH:23][CH:24]=[CH:25]2)[CH:20]=1)[C:14]([N:4]=[C:3]([NH2:5])[NH2:2])=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 18945167HCID 18945167, compound

Product 1

HCID 18945428HCID 18945428, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of guanidine hydrochloride (62.1 g) in N,N-dimethylformamide (150 ml) was added 28% sodium methoxide in methanol (106 ml) under nitrogen. After being stirred for 30 minutes at room temperature, to the reaction mixture was added a solution of methyl 3-hydroxymethyl-5-(pyrrol-1-yl)benzoate (30.0 g) in N,N-dimethylformamide (150 ml). After being stirred for 21 hours at room temperature, the reaction mixture was poured into water (1.5 l) with stirring. The resulting precipitate was collected by filtration, washed with water and purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was dissolved in ethanol (70 ml) and crystallized from slight excess 4N-hydrogen chloride-ethyl acetate. The crystalline was recrystallized from an aqueous ethanol to afford 2-[3-hydroxymethyl-5-(pyrrol-1-yl)benzoyl]guanidine hydrochloride (7.3 g).

Workup

  1. stirringAfter being stirred for 21 hours at room temperature
  2. stirringwith stirring
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. custompurified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1)
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo
  9. dissolutionThe residue was dissolved in ethanol (70 ml)
  10. customcrystallized from slight excess 4N-hydrogen chloride-ethyl acetate
  11. customThe crystalline was recrystallized from an aqueous ethanol

Sources & evidence

ORD record
ord-9a3b099ca35446509e0284cb1b08f0c5
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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