Acetic Acid → 5-Oxo-2,2,4-trimethyl-3-thiazoline oxime

HRID 1981375Notes

Reaction equation

HRID 1981375 reaction equation
[CH3:1][C:2]1([CH3:8])[N:6]=[C:5]([CH3:7])[CH2:4][S:3]1.[N:9]([O-])=[O:10].[Na+].C(O)(=O)C>O>[N:9](=[C:4]1[S:3][C:2]([CH3:8])([CH3:1])[N:6]=[C:5]1[CH3:7])[OH:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 850553-Thiazoline, 2,2,4-trimethyl-HCID 23668193Sodium Nitrite

Product 1

HCID 1362290545-Oxo-2,2,4-trimethyl-3-thiazoline oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

30.0 g (0.232 mol) of 2,2,4-trimethyl-3-thiazoline and 17.6 g (0.255 mol) of sodium nitrite are dissolved in 75 ml of water and 26.6 ml (0.464 mol) of acetic acid are added dropwise, with stirring at 45° C. The internal temperature of the reaction mixture is allowed to rise slowly to 10°-15° C., and the mixture is then stirred at this temperature for an additional 2 hours. The product precipitates as ochre-brown crystals and is filtered, washed with water and dried in vacuo. A single recrystallization from chloroform/n-hexane yields 5-oxo-2,2,4-trimethyl-3-thiazoline oxime, m.p. 159°-161° C.

Workup

  1. customto rise slowly to 10°-15° C.
  2. stirringthe mixture is then stirred at this temperature for an additional 2 hours
  3. customThe product precipitates as ochre-brown crystals
  4. filtrationis filtered
  5. washwashed with water
  6. customdried in vacuo
  7. customA single recrystallization from chloroform/n-hexane

Sources & evidence

ORD record
ord-b87b0350667b4bc480fb42e24eb62e92
Source dataset
uspto-grants-1985_04
Patent number
US04514566

Reaction notes

Loading…