2H-1,2,4,6-Thiatriazine, 3-chloro-2-ethyl-5-methyl-, 1,1-dioxide → HCID 15583449, compound

HRID 2296238Notes

Reaction equation

HRID 2296238 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:6]([CH2:14][CH3:15])[S:7](=[O:13])(=[O:12])[N:8]=[C:9]([CH3:11])[N:10]=1>O1CCCC1>[CH2:14]([N:6]1[C:5]([O:2][CH3:1])=[N:10][C:9]([CH3:11])=[N:8][S:7]1(=[O:13])=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 1588662H-1,2,4,6-Thiatriazine, 3-chloro-2-ethyl-5-methyl-, 1,1-dioxideHCID 10942334Sodium Methoxide

Product 1

HCID 15583449HCID 15583449, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

19.8 parts of 30 percent strength sodium methylate were added to a solution of 20.95 parts of 3-chloro-2-ethyl-5-methyl-2H-1,2,4,6-thiatriazine-1,1-dioxide in 120 parts of tetrahydrofuran at 20°-25° C. in the course of 10 minutes, while stirring. The reaction mixture was stirred for three hours at 25° C. and then concentrated, the residue was taken up in ethyl acetate, and the solution was extracted twice with dilute sodium carbonate solution. The organic phase was separated off, dried and chromatographed over silica gel. The solution was then concentrated under reduced pressure, giving 14.5 parts of 2-ethyl-5-methyl-3-methoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide of melting point 50°-53° C.

Workup

  1. stirringThe reaction mixture was stirred for three hours at 25° C.
  2. concentrationconcentrated
  3. extractionthe solution was extracted twice with dilute sodium carbonate solution
  4. customThe organic phase was separated off
  5. customdried
  6. customchromatographed over silica gel
  7. concentrationThe solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e6b3b89e55e4875899c588bb67a7e6d
Source dataset
uspto-grants-1984_01
Patent number
US04428766

Reaction notes

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