Sulfuric acid magnesium salt (1:1) → 3-(5-Chloro-2-thienyl)-5,6-dihydro-1,4,2-oxathiazine-4,4-dioxide

HRID 841852

Reaction equation

HRID 841852 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2S[CH2:11][CH2:10][O:9][N:8]=2)=[CH:4][CH:3]=1.[S:13]([O-:17])([O-])(=O)=[O:14].[Mg+2].ClC1C=C(C=CC=1)C(OO)=O>C=Cl.C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]2[S:13](=[O:17])(=[O:14])[CH2:11][CH2:10][O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 70297m-Chloroperbenzoic acidHCID 226173463-(5-Chloro-2-thienyl)-5,6-dihydro-1,4,2-oxathiazine

Product 1

HCID 226173603-(5-Chloro-2-thienyl)-5,6-dihydro-1,4,2-oxathiazine-4,4-dioxideYield 103.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 5378701Methyl, chloro-Solvent

Conditions

Temperature
30 °C

Procedure

3-(5-Chloro-2-thienyl)-5,6-dihydro-1,4,2-oxathiazine (12g, 0.055 mol) prepared in Example 1, in methylene chlorine (50 ml) and anhydrous magnesium sulphate (10 g) in suspension, was stirred while m-chloroperoxybenzoic acid (34g, 50-60% material) in methylene chloride (250 ml), was added dropwise, to prepare a reaction mixture. The reaction mixture was allowed to warm to 30° C. and after the dropwise addition was externally heated to 35° C. for 10 hours by which time a negative starch/Kl test was obtained. Unwanted m-chlorobenzoic acid was then removed from the reaction mixture by extraction with aqueous sodium bicarbonate. The remaining reaction mixture was washed with water, dried (MgSO4) and evaporated to dryness. The resultant residue was chromatographed on 500 g silica gel eluting with methylene chloride, to produce 3-(5-chloro-2-thienyl)-5,6-dihydro-1,4,2-oxathiazine-4,4-dioxide (mp 113-114° C., 14.3g, Found: C 33.27, H 2.33, N 5.55; C7H6ClNO3S2 requires C 33.40, H 2.39, N 5.57).

Workup

  1. additionwas added dropwise
  2. customto prepare a reaction mixture
  3. additionafter the dropwise addition
  4. customwas obtained
  5. customUnwanted m-chlorobenzoic acid was then removed from the reaction mixture by extraction with aqueous sodium bicarbonate
  6. customThe remaining reaction mixture
  7. washwas washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness
  10. customThe resultant residue was chromatographed on 500 g silica gel eluting with methylene chloride

Sources & evidence

ORD record
ord-8164493e8a174649aa9bc3e6d25bac6f
Source dataset
uspto-grants-2002_04
Patent number
US06372297B1

Linked notes

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