Formamidine acetate → HCID 178521435, compound

HRID 1007932Notes

Reaction equation

HRID 1007932 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][C:15]=1[NH2:16])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].[C:17](O)(=O)C.C(N)=N>COCCO>[NH:16]1[C:15]2[CH:14]=[CH:13][C:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12])=[CH:5][C:4]=2[N:3]=[CH:17]1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 22666387HCID 22666387, compound

Product 1

HCID 178521435HCID 178521435, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

In 10 mL of ethylene glycol monomethyl ether is dissolved 1.2 g of 2-[(3,4-diaminophenethyl)oxy]-1-ethanol dihydrochloride, to which is added 0.93 g of formamidine acetate. The mixture is heated under reflux for 30 minutes. Then, the solvent is distilled off under reduced pressure, water and methylene chloride are added to the residue, pH is adjusted to 9 with 2 mol/L aqueous solution of sodium hydroxide, and the organic layer is separated. The aqueous layer is salted out and extracted with methylene chloride. The organic layers are collected, washed with saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: chloroform:methanol=10:1) to obtain 0.52 g of 2-[2-(1H-benzo[d]imidazol-5-yl)ethoxy]-1-ethanol as an oily product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 30 minutes
  3. distillationThen, the solvent is distilled off under reduced pressure, water and methylene chloride
  4. additionare added to the residue, pH
  5. customthe organic layer is separated
  6. extractionextracted with methylene chloride
  7. customThe organic layers are collected
  8. washwashed with saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent is distilled off under reduced pressure
  11. customthe residue is purified by column chromatography (eluent: chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-971d8ef7305448beb46a8c6eb4f1f2fc
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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