Guanidine Hydrochloride → HCID 178483836, compound

HRID 1740320Notes

Reaction equation

HRID 1740320 reaction equation
[C:1](/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([C:16]2[CH:20]=[C:19]([Cl:21])[S:18][C:17]=2[Cl:22])[CH:9]=[C:10]([CH:15]=1)[C:11]([O:13]C)=O)([OH:3])=O.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27].ON1C2C=CC=CC=2N=N1.[ClH:39].CN(C)CCCN=C=NCC.Cl.[NH2:52][C:53]([NH2:55])=[NH:54].C[O-].[Na+]>CN(C)C=O>[ClH:21].[ClH:39].[Cl:22][C:17]1[S:18][C:19]([Cl:21])=[CH:20][C:16]=1[C:8]1[CH:9]=[C:10]([CH:15]=[C:6](/[CH:5]=[CH:4]/[C:1](=[O:3])[NH:27][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])[CH:7]=1)[C:11]([NH:54][C:53]([NH2:55])=[NH:52])=[O:13]

Participants

8

Reactant 6

HCID 5742Guanidine HydrochlorideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10942334Sodium MethoxideHCID 21838118HCID 21838118, compound

Product 1

HCID 178483836HCID 178483836, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The mixture of methyl 5-[(E)-2-carboxyethenyl]-3-(2,5-dichlorothiophen-3-yl)benzoate (0.6 g), N,N-dimethylethylenediamine (0.22 ml), 1-hydroxy-benzotriazole (0.27 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.35 g) in N,N-dimethylformamide (10 ml) was stirred for 4 hours at ambient temperature. To the above mixture was added a mixture of guanidine hydrochloride (0.8 g) in N,N-dimethylformamide (10 ml) and 28 methanolic sodium methoxide (1.5 ml). The mixture was stirred for 16 hours at same temperature and the mixture was poured onto water. The mixture was extracted with the solution of ethyl acetate and tetrahydrofuran and the extracted layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. To the residue in methanol (10 ml) was added slight excess 4N-hydrogen chloride-ethyl acetate, and the isolated precipitate was collected by filtration. The precipitate was recrystallized from methanol to give [3-(2,5-dichlorothiophen-3-yl)-5-[(E)-2-[(2-dimethylaminoethyl)carbamoyl]ethenyl]benzoyl]guanidine dihydrochloride (0.44 g).

Workup

  1. additionTo the above mixture was added
  2. stirringThe mixture was stirred for 16 hours at same temperature
  3. additionthe mixture was poured onto water
  4. extractionThe mixture was extracted with the solution of ethyl acetate and tetrahydrofuran
  5. washthe extracted layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. additionTo the residue in methanol (10 ml) was added slight excess 4N-hydrogen chloride-ethyl acetate
  9. filtrationthe isolated precipitate was collected by filtration
  10. customThe precipitate was recrystallized from methanol

Sources & evidence

ORD record
ord-88d5071c1fcd4a84b501295d4dab3dcb
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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