Water → HCID 178419031, compound

HRID 1816228Notes

Reaction equation

HRID 1816228 reaction equation
O1CCOCC1.Cl.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:23]#[C:24][NH2:25].O>CCOCC>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([NH:19][C:24]([NH2:25])=[NH:23])[CH:20]=[CH:21][CH:22]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9864CyanamideHCID 928923-BenzyloxyanilineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 178419031HCID 178419031, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A 4 N HCl dioxane suspension of 3-benzyloxyaniline (1.0 equivalent) and cyanamide (1.0 equivalent) was stirred at 100° C. overnight. To the reaction mixture was added water and ether. The aqueous layer was washed with ether twice. The aqueous layer was adjusted to a pH greater 10 with 1M NaOH, and the desired guanidine was extracted to methylene chloride, precipitated and filtered. The filtration cake was N-(3-benzyloxy-phenyl)-guanidine (greater than 80% yield).

Workup

  1. washThe aqueous layer was washed with ether twice
  2. extractionthe desired guanidine was extracted to methylene chloride
  3. customprecipitated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e34249b3653449c18f2d0f84430a8096
Source dataset
uspto-grants-2005_04
Patent number
US06884804B2

Reaction notes

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