Ammonia → 6-(Hydroxyimino)-5,5-dimethylthiomorpholin-3-one

HRID 1834878Notes

Reaction equation

HRID 1834878 reaction equation
C([O:3][C:4]([CH2:6][S:7][C:8](=[N:15][OH:16])[C:9]([N+:12]([O-])=O)([CH3:11])[CH3:10])=O)C.[OH-].[NH4+].N>O>[N:15](=[C:8]1[C:9]([CH3:11])([CH3:10])[NH:12][C:4](=[O:3])[CH2:6][S:7]1)[OH:16]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 867354161-Ethoxycarbonylmethylthio-2-nitro-2-methylpropionaldoxime

Product 1

HCID 713869496-(Hydroxyimino)-5,5-dimethylthiomorpholin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12 g. of 1-ethoxycarbonylmethylthio-2-nitro-2-methylpropionaldoxime and 150 ml of ammonium hydroxide was charged into a pyrex pressure bottle and stirred at room temperature for three days. The excess ammonia and water was stripped from the reaction mixture under reduced pressure. The solid crystalline residue was washed with a small amount of cold water and dried. The residue was then recrystallized from acetonitrile to yield 4 g of 2-Oximino-3,3-dimethyltetrahydro-1,4-thiazin-5-one, m.p. 234°-236° C. The nmr and infrared spectra supported the proposed structure.

Workup

  1. additionA mixture of 12 g
  2. washThe solid crystalline residue was washed with a small amount of cold water
  3. customdried
  4. customThe residue was then recrystallized from acetonitrile

Sources & evidence

ORD record
ord-459a67e7a945447bb1eb2c4dae9194bb
Source dataset
uspto-grants-1978_01
Patent number
US04071627

Reaction notes

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