Methanol → HCID 178491252, compound

HRID 860180Notes

Reaction equation

HRID 860180 reaction equation
C(N)C1C=CC=CC=1.[NH2:9][NH:10][C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[NH:12].[Cl:21][C:22]1[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][C:23]=1[CH:24]=O.CO>C(O)C>[Cl:21][C:22]1[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][C:23]=1[CH:24]=[N:9][NH:10][C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[NH:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 7504BenzylamineHCID 794452-ChloroveratraldehydeHCID 178513140HCID 178513140, compound

Product 1

HCID 178491252HCID 178491252, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

536 mg (5 mmol) benzylamine and 1.17 g (5 mmol) S′-methylthiosemicarbazide hydroiodide was mixed in 10 ml of ethanol. The reaction mixture was refluxed for 5 minutes after which it was cooled down to room temperature and the residue filtered off. The crude product of N-amino-N′-benzylguanidine was reacted with 1.0 g (5 mmol) 2-chloro-3,4-dimethoxybenzaldehyde under reflux for 5 h, after which the solvent was removed under vacuum to give a white solid. The product was obtained by recrystallisation from methanol. Yield of title compound 1, was 1.65 g (77%). M.p. 0.223–225° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 minutes after which it
  2. filtrationthe residue filtered off
  3. temperatureunder reflux for 5 h
  4. customafter which the solvent was removed under vacuum
  5. customto give a white solid

Sources & evidence

ORD record
ord-e3ed2de675fe4f90a8bd5a9256dc2f41
Source dataset
uspto-grants-2006_12
Patent number
US07153881B2

Reaction notes

Loading…