Guanidine Hydrochloride → HCID 178479491, compound

HRID 1740318Notes

Reaction equation

HRID 1740318 reaction equation
[ClH:1].[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].[C:9]1([C:19]2[CH:20]=[C:21]([CH:37]=[CH:38][CH:39]=2)[C:22](OCC(C)(NS(C(F)(F)F)(=O)=O)C)=[O:23])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]=1.C(OCC)(=O)C>CN(C)C=O.O>[ClH:1].[C:9]1([C:19]2[CH:20]=[C:21]([CH:37]=[CH:38][CH:39]=2)[C:22]([NH:4][C:3]([NH2:5])=[NH:2])=[O:23])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]=1

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 54332867HCID 54332867, compound

Product 1

HCID 178479491HCID 178479491, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of guanidine hydrochloride (0.87 g) in N,N-dimethylformamide (5 ml) was added sodium methoxide (1.6 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-(3,4-dihydro-1-naphthyl)benzoate (0.59 g) in N,N-dimethylformamide (5 ml). After being stirred for 21 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 dissolved in ethyl acetate and crystallized from slight excess 4N-hydrogen chloride-ethyl acetate. The crystalline was triturated with diethyl ether to give [3-(3,4-dihydro-1-naphthyl)benzoyl]guanidine hydrochloride (0.25 g).

Workup

  1. stirringAfter being stirred for 21 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. dissolutionthe residue was dissolved in ethyl acetate
  6. customcrystallized from slight excess 4N-hydrogen chloride-ethyl acetate
  7. customThe crystalline was triturated with diethyl ether

Sources & evidence

ORD record
ord-806d712d9f814aadbe2ed7ee0645cd91
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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