Potassium Hydroxide → HCID 54291157, compound

HRID 1758042Notes

Reaction equation

HRID 1758042 reaction equation
[CH:1]([N:3]1[C:8]([C:9](=[N:15][O:16][CH3:17])[C:10]([O:12]CC)=[O:11])=[CH:7][S:6][CH2:5][CH2:4]1)=[O:2].[OH-].[K+]>C(O)C>[CH:1]([N:3]1[C:8]([C:9](=[N:15][O:16][CH3:17])[C:10]([OH:12])=[O:11])=[CH:7][S:6][CH2:5][CH2:4]1)=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54041192HCID 54041192, compound

Product 1

HCID 54291157HCID 54291157, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of thus obtained ethyl 2-(4-formyl-2,3-dihydro-4H-1,4-thiazin-5-yl)-2-methoxyiminoacetate (syn isomer, 4.8 g.) in ethanol (48 ml.) was added 1 N aqueous solution of potassium hydroxide (22.3 ml.), and the mixture was stirred at room temperature for 1.25 hours. After removing ethanol from the resultant solution under reduced pressure, water was added to the residue to a total volume of 100 ml., and washed with diethyl ether. The solution was adjusted to pH 1 with 10% hydrochloric acid, and salted out. After the solution was extracted with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether (15 ml.) and the crystals were collected by filtration and washed with diethyl ether to give 2-(4-formyl-2,3-dihydro-4H-1,4-thiazin-5-yl)-2-methoxyiminoacetic acid (syn isomer, 3.51 g.).

Workup

  1. customAfter removing ethanol from the resultant solution under reduced pressure, water
  2. additionwas added to the residue to a total volume of 100 ml
  3. wash, and washed with diethyl ether
  4. extractionAfter the solution was extracted with ethyl acetate
  5. washthe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with diethyl ether (15 ml.)
  9. filtrationthe crystals were collected by filtration
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ce50cf40187948748009af1f00c6583c
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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