Stannous chloride dihydrate → HCID 178485146, compound

HRID 565042Notes

Reaction equation

HRID 565042 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([N:23]=[C:24]([NH2:27])[NH:25][CH3:26])=[O:22])[NH:6]2.O.O.[Sn](Cl)Cl.O.N>C(O)C>[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][C:9]1[CH:8]=[C:7]2[C:3]([CH:4]=[C:5]([C:21]([N:23]=[C:24]([NH2:27])[NH:25][CH3:26])=[O:22])[NH:6]2)=[C:2]([Cl:1])[CH:10]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 12896473Azane;hydrateHCID 178485148HCID 178485148, compound

Product 1

HCID 178485146HCID 178485146, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 0.23 g (0.60 mmol) of 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indoloylguanidine, 0.72 g (3.20 mmol) of tin (II) chloride dihydrate and 15 ml of ethanol was heated to reflux for 3 hours. After cooling, 28% ammonia water was added to the reaction mixture and ethanol was then distilled off under reduced pressure. The residue was extracted three times with ethyl acetate. The combined extracts were then washed with saturated sodium chloride aqueous solution. 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 0.11 g (51.6%) of 6-(2-aminophenoxy)-4-chloro-1-methyl-2-indoloylguanidine. The product was converted into the hydrochloride with hydrogen chloride/methanol to give 0.097 g of 6-(2-aminophenoxy)-4-chloro-1-methyl-2-indoloylguanidine hydrochloride.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooling
  4. distillationwas then distilled off under reduced pressure
  5. extractionThe residue was extracted three times with ethyl acetate
  6. washThe combined extracts were then washed with saturated sodium chloride aqueous solution
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was isolated
  10. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ec1c12a30cf417e9b5c318a23ead021
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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