Sodium Chloride → HCID 136365308, compound

HRID 2395361Notes

Reaction equation

HRID 2395361 reaction equation
[O:1]=[C:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]([O:16]CC)=O)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.C[O-].[Na+].Cl.[NH2:23][C:24]([NH2:26])=N.[Cl-].[Na+].C[N:30](C)C=O>>[NH2:30][N:23]=[CH:24][NH:26][C:14]([C:6]1[NH:7][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:2](=[O:1])[CH2:3][CH2:4][C:5]=1[C:13]=23)=[O:16]

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 5742Guanidine HydrochlorideHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 12377168HCID 12377168, compound

Product 1

HCID 136365308HCID 136365308, compound

Procedure

A mixture of ethyl 1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxylate (1.00 g, 4.11 mmol), sodium methoxide (2.22 g, 41.1 mmol), guanidine hydrochloride (3.92 g, 41.1 mmol) and N,N-dimethylformamide (15 ml) was stirred overnight at room temperature. After completion of the reaction, a 5% aqueous sodium chloride solution was added to the reaction mixture under ice-cooling, followed by extraction with ethyl acetate (three times). The extract solution was washed twice with a 5% aqueous sodium hydrogencarbonate solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=95/5) to obtain N-(aminoiminomethyl) -1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxamide (1.00 g). This compound (1.00 g) was treated with a mixture of isopropanol/water and methanesulfonic acid (0.75 g, 7.80 mmol) to obtain crude N-(aminoiminomethyl)-1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxamide methanesulfonate. This crude product was recrystallized from methanesulfonic acid (0.04 g, 0.39 mmol) and water (36 ml) to obtain N-(aminoiminomethyl)-1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxamide methanesulfonate (0.72 g).

Workup

  1. customAfter completion of the reaction
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate (three times)
  4. washThe extract solution was washed twice with a 5% aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-f93d0171446f4cb1a6c62981b8030ca5
Source dataset
uspto-grants-1998_09
Patent number
US05814654

Reaction notes

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