Sodium Hydroxide → N-amidinoisooxazolidine sulfate

HRID 1733443Notes

Reaction equation

HRID 1733443 reaction equation
Cl.[O:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.[OH-].[Na+].[S:9]([OH:13])([OH:12])(=[O:11])=[O:10].CS[C:16](=[NH:18])[NH2:17]>O>[S:9]([OH:13])([OH:12])(=[O:11])=[O:10].[C:16]([N:3]1[CH2:4][CH2:5][CH2:6][O:2]1)(=[NH:17])[NH2:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 12304500Isoxazolidine hydrochloride

Product 1

HCID 20465274N-amidinoisooxazolidine sulfate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 14.5 g. (0.13 mole) of isooxazolidine hydrochloride in water (100 ml.) is added 10.4 g. (0.13 mole) of fifty percent (w/w) aqueous sodium hydroxide and the mixture stirred for fifteen minutes. To this solution is added 18.1 g. (0.065 moles) of 2 -methyl-2-thiopseudourea sulfate and the entire mixture stirred under a stream of nitrogen overnight. The mixture is refluxed for 11/2, hours then filtered while still hot. The water is removed under vacuum to give a semi-solid residue which is triturated with hot isopropanol (3×100 ml.). The isopropanol is removed under vacuum to give an oil which is crystallized from isopropanol to give N-amidinoisooxazolidine sulfate.

Workup

  1. additionTo this solution is added 18.1 g
  2. temperatureThe mixture is refluxed for 11/2, hours
  3. filtrationthen filtered while still hot
  4. customThe water is removed under vacuum
  5. customto give a semi-solid residue which
  6. customis triturated with hot isopropanol (3×100 ml.)
  7. customThe isopropanol is removed under vacuum
  8. customto give an oil which
  9. customis crystallized from isopropanol

Sources & evidence

ORD record
ord-3d12e1f9f2b14320979b0bc99ead82b0
Source dataset
uspto-grants-1980_12
Patent number
US04242337

Reaction notes

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