Water → N-(Phenylmethoxy)guanidine

HRID 1439220Notes

Reaction equation

HRID 1439220 reaction equation
S([O-])([O-])(=O)=O.CS[C:8]([NH2:10])=[NH2+:9].CSC(N)=[NH2+].O.[CH2:17]([O:24][NH2:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[CH2:17]([O:24][NH:25][C:8]([NH2:10])=[NH:9])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 102313O-BenzylhydroxylamineHCID 6604939S-methyl isothiourea hemisulfate

Product 1

HCID 178513190N-(Phenylmethoxy)guanidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 30.0 g. (0.12 moles) of S-methylthiouronium sulfate in 200 ml. of H2O there is added a solution of 24.6 g. (0.20 moles) of benzyloxyamine in 250 ml. of 95% ethanol. The mixture is stirred for 72 hours at room temperature. The clear solution is heated at reflux for two hours under a stream of nitrogen. The solvents are removed in vacuo and the residue is treated with 300 ml. of isopropanol. The solid is removed by filtration and dissolved in 300 ml. of water. The solution is made basic with 90 ml. of 10% aqueous sodium hydroxide. The precipitate is collected, washed with water and dried to give benzyloxyguanidine, m.p. 104°-5° C.

Workup

  1. temperatureThe clear solution is heated
  2. temperatureat reflux for two hours under a stream of nitrogen
  3. customThe solvents are removed in vacuo
  4. additionthe residue is treated with 300 ml
  5. customThe solid is removed by filtration
  6. dissolutiondissolved in 300 ml
  7. customThe precipitate is collected
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-93a659487d2343829c7ec7728acc70af
Source dataset
uspto-grants-1977_11
Patent number
US04058557

Reaction notes

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