Guanidine Hydrochloride → HCID 178479490, compound

HRID 1067800Notes

Reaction equation

HRID 1067800 reaction equation
[ClH:1].[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].[CH2:9]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25](OCC3C=CC=CC=3)=[O:26])=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[ClH:1].[CH2:9]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([NH:4][C:3]([NH2:5])=[NH:2])=[O:26])=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10664938HCID 10664938, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 178479490HCID 178479490, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

After 2.24 g (23.4 mmol) of guanidine hydrochloride was added to 50 ml of a methanol solution of 1.26 g (23.4 mmol) of sodium methoxide, 0.80 g (2.34 mmol) of benzyl 1-benzyl-5-indolecarboxylate was added to the resulting mixture. The mixture was then stirred for 30 hours while heating at 50 to 60° C. Methanol was distilled off under reduced pressure and the residue was purified by silica gel column chromatography followed by treatment with 2N hydrochloric acid to give 0.08 g (10.4%) of 1-benzyl-5-indoloylguanidine hydrochloride.

Workup

  1. additionwas added to the resulting mixture
  2. distillationMethanol was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-03717aa71ebf411fa6205b5d2131fca4
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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