Guanidine Hydrochloride → HCID 9818000, compound

HRID 399864Notes

Reaction equation

HRID 399864 reaction equation
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].[CH3:9][S:10]([C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([N:23]2[CH:27]=[CH:26][CH:25]=[CH:24]2)[CH:22]=1)[C:16](OC)=[O:17])(=[O:12])=[O:11]>CO>[CH3:9][S:10]([C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([N:23]2[CH:27]=[CH:26][CH:25]=[CH:24]2)[CH:22]=1)[C:16]([N:7]=[C:6]([NH2:8])[NH2:5])=[O:17])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 18945432Methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate

Product 1

HCID 9818000HCID 9818000, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

28% Methanolic sodium methoxide (6.2 ml) was added to a solution of guanidine hydrochloride (3.2 g) in dry methanol (40.0 ml) and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate (1.9 g) and the mixture was stirred for 7 hours at the same temperature. The solvent was removed by concentration and the residue was added to a mixture of ethyl acetate, tetrahydrofuran and water. The separated organic layer was washed with brine and dried over magnesium sulfate. The residue was obtained by evaporating a solvent, and purified by column chromatography on alumina eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired product were collected and evaporated in vacuo. The residue was recrystallized from a mixture of methanol and diisopropyl ether to give 2-[3-methylsulfonyl-5-(pyrrol-1-yl)benzoyl]guanidine (0.44 g).

Workup

  1. stirringthe mixture was stirred for 7 hours at the same temperature
  2. customThe solvent was removed by concentration
  3. additionthe residue was added to a mixture of ethyl acetate, tetrahydrofuran and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe residue was obtained
  7. customby evaporating a solvent
  8. custompurified by column chromatography on alumina eluting with a mixture of chloroform and methanol (19:1, V/V)
  9. additionThe fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo
  12. customThe residue was recrystallized from a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-cb47ea8cb90446498f95effb0ba4a1e0
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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