Guanidine Hydrochloride → HCID 178505357, compound

HRID 1740319Notes

Reaction equation

HRID 1740319 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].[CH2:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:19]=[C:20]([CH:36]=[CH:37][CH:38]=2)[C:21](OCC(C)(N[S:28]([C:31](F)(F)F)(=[O:30])=[O:29])C)=[O:22])=[CH:10]1.C(OCC)(=[O:41])C>CN(C)C=O.O>[CH3:31][S:28]([OH:41])(=[O:30])=[O:29].[CH2:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:19]=[C:20]([CH:36]=[CH:37][CH:38]=2)[C:21]([NH:4][C:3]([NH2:5])=[NH:2])=[O:22])=[CH:10]1

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 54180626HCID 54180626, compound

Product 1

HCID 178505357HCID 178505357, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of guanidine hydrochloride (1.54 g) in N,N-dimethylformamide (5 ml) was added sodium methoxide (2.8 ml, 28% in methanol) under nitrogen atmosphere. After being stirred for 30 minutes at room temperature, to the reaction mixture was added a solution of 2-methyl-2-trifluoromethylsulfonylaminopropyl 3-(1H-inden-3-yl)benzoate (1.01 g) in N,N-dimethylformamide (5 ml). After being stirred for 23 hours at room temperature, the reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was successively washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was 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 and crystallized from slight excess methanesulfonic acid. The crystalline was recrystallized from ethanol to give [3-(1H-inden-3-yl)benzoyl]guanidine methanesulfonate (0.22 g).

Workup

  1. stirringAfter being stirred for 23 hours at room temperature
  2. washThe organic layer was successively washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified 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
  10. customcrystallized from slight excess methanesulfonic acid
  11. customThe crystalline was recrystallized from ethanol

Sources & evidence

ORD record
ord-7a2ef5a546834275b933eb7246d7d86c
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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