Guanidine Hydrochloride → HCID 178483822, compound

HRID 850321Notes

Reaction equation

HRID 850321 reaction equation
[ClH:1].[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].Cl.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[C:18]1[CH:19]=[C:20]([C:28](=[O:35])[NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH:21]=[C:22]([CH:27]=1)[C:23](OC)=[O:24]>CN(C)C=O.C(OCC)(=O)C.O1CCCC1.O>[ClH:10].[ClH:1].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[C:18]1[CH:19]=[C:20]([C:28](=[O:35])[NH:29][CH2:30][CH2:31][N:32]([CH3:33])[CH3:34])[CH:21]=[C:22]([CH:27]=1)[C:23]([NH:4][C:3]([NH2:5])=[NH:2])=[O:24]

Participants

8

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 70250203HCID 70250203, compound

Product 1

HCID 178483822HCID 178483822, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of guanidine.hydrochloride (0.4 g) in N,N-dimethylformamide (7.2 ml) was added sodium methoxide (0.76 ml, 28% in methanol) under nitrogen atmosphere. After being stirred for 15 minutes at room temperature, to the reaction mixture was added methyl 5-(2,5-dichlorophenyl)-3-[(2-dimethylaminoethyl)carbamoyl]benzoate.hydrochloride (0.36 g). After being stirred for 4 hours at room temperature, the residue was dissolved in a mixture of ethyl acetate (40 ml), tetrahydrofuran (20 ml) and water (40 ml). The aqueous layer was further extracted with a mixture of ethyl acetate (40 ml) and tetrahydrofuran (20 ml). The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in ethanol (8 ml) and added slightly excess 4N hydrochloride in dioxane to afford [5-(2,5-dichlorophenyl)-3-[(2-dimethylaminoethyl)carbamoyl]benzoyl]guanidine.dihydrochloride.

Workup

  1. stirringAfter being stirred for 4 hours at room temperature
  2. extractionThe aqueous layer was further extracted with a mixture of ethyl acetate (40 ml) and tetrahydrofuran (20 ml)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in ethanol (8 ml)
  7. additionadded slightly excess 4N hydrochloride in dioxane

Sources & evidence

ORD record
ord-be9c40db16d14e61b4470bdcd7243b6d
Source dataset
uspto-grants-2000_01
Patent number
US06017917

Reaction notes

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