Guanidine Hydrochloride → HCID 178485148, compound

HRID 1067828Notes

Reaction equation

HRID 1067828 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[CH3:6][O-].[Na+].[Cl:9][C:10]1[CH:18]=[C:17]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-:28])=[O:27])[CH:16]=[C:15]2[C:11]=1[CH:12]=[C:13]([C:30](OCC)=[O:31])[N:14]2C>CO>[Cl:9][C:10]1[CH:18]=[C:17]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-:28])=[O:27])[CH:16]=[C:15]2[C:11]=1[CH:12]=[C:13]([C:30]([N:4]=[C:3]([NH2:5])[NH:2][CH3:6])=[O:31])[NH:14]2

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 21194137Ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate

Product 1

HCID 178485148HCID 178485148, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 2.87 g (30.0 mmol) of guanidine hydrochloride was added to 25 ml of a methanol solution of 1.62 g (30.0 mmol) of sodium methoxide, the mixture was stirred at room temperature for 30 minutes. The precipitated sodium chloride was filtered off. To the obtained solution was added 0.51 g (1.50 mmol) of ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate. Subsequently methanol was distilled off under reduced pressure. The resulting residue was heated at 130° C. for 5 minutes and then allowed to stand at room temperature for an hour. Thereafter water was poured onto the reaction solution and the mixture was extracted three times with ethyl acetate. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was isolated and purified by silica gel column chromatography to give 0.23 g (40.1%) of 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indoloylguanidine.

Workup

  1. filtrationThe precipitated sodium chloride was filtered off
  2. distillationSubsequently methanol was distilled off under reduced pressure
  3. temperatureThe resulting residue was heated at 130° C. for 5 minutes
  4. waitto stand at room temperature for an hour
  5. additionThereafter water was poured onto the reaction solution
  6. extractionthe mixture was extracted three times with ethyl acetate
  7. washThe combined extracts were washed with water
  8. dry with materialAfter drying over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resulting residue was isolated
  11. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-13ccadf78e7c46eb8a96190fdd7dca03
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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