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

HRID 1955950

반응식

HRID 1955950 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 5378701Methyl, chloro-용매

반응 조건

온도
30 °C

실험 절차

3-(5-Chloro-2-thienyl)-5,6-dihydro-1,4,2-oxathiazine (12 g, 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 (34 g, 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., 14.3 g, Found: C 33.27, H 2.33, N 5.55; C7H6ClNO3S2 requires C 33.40, H 2.39, N 5.57).

후처리

  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

출처 및 근거

ORD 기록
ord-d7aacc947e924e50a699a250de1c330b
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05777110

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