3,5-Dichloro-4H-1,2,6-thiadiazin-4-one → 3-Chloro-5-methoxy-4H-1,2,6-thiadiazin-4-one

HRID 615128Notes

Reaction equation

HRID 615128 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[C:6](Cl)=[N:5][S:4][N:3]=1.[CH3:10][O-:11].[Na+]>CO>[Cl:1][C:2]1[C:7](=[O:8])[C:6]([O:11][CH3:10])=[N:5][S:4][N:3]=1

Participants

4

Reactant 2

HCID 3540263,5-Dichloro-4H-1,2,6-thiadiazin-4-oneHCID 10942334Sodium Methoxide

Product 1

HCID 155937013-Chloro-5-methoxy-4H-1,2,6-thiadiazin-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3.66 g of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one in 30 ml of methanol is kept at 0°-5° C. and stirred while a solution of 2.40 g of sodium methoxide in 30 ml of methanol is added dropwise to it. The reaction mixture is stirred at room temperature 2 hours longer, then mixed with 200 ml of ice water. The precipitate is collected, washed with water, dried, and recrystallized from hexane to yield pale yellow needles, mp 159°-161°.

Workup

  1. customis kept at 0°-5° C.
  2. additionis added dropwise to it
  3. customThe precipitate is collected
  4. washwashed with water
  5. customdried
  6. customrecrystallized from hexane
  7. customto yield pale yellow needles, mp 159°-161°

Sources & evidence

ORD record
ord-957ce57639f84af5bd4c753ac943f833
Source dataset
uspto-grants-1985_02
Patent number
US04497807

Reaction notes

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