m-Chloroperbenzoic acid → HCID 13577567, compound

HRID 653008Notes

Reaction equation

HRID 653008 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:13][CH2:12][CH2:11][O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:19].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:13](=[O:19])[CH2:12][CH2:11][O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 13577522HCID 13577522, compound

Product 1

HCID 13577567HCID 13577567, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

5,6-Dihydro-3-(3-fluorophenyl)-1,4,2-oxathiazine (19.7 g, 0.1 mol) was dissolved in chloroform, 50 ml). 3-Chloroperoxybenzoic acid (21 g) dissolved in chloroform (200 ml) was added dropwise at such a rate that the temperature of the reaction mixture remained at between 25° to 30° C. After the addition was complete, the reaction was left stirring at room temperature overnight. Saturated aqueous sodium bicarbonate was added and stirred until all gassing ceased. The chloroform solution was washed with water, dried over anhydrous magnesium sulphate and evaporated to leave a solid which was recrystallised from ether/ligroin, to give 5,6-dihydro-3-(3-fluorophenyl)-1,4,2-oxathiazine 4-oxide, mp 79° C.

Workup

  1. additionwas added dropwise at such a rate that the temperature of the reaction mixture
  2. customremained at between 25° to 30° C
  3. additionAfter the addition
  4. waitthe reaction was left
  5. stirringstirred until all gassing
  6. washThe chloroform solution was washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated
  9. customto leave a solid which
  10. customwas recrystallised from ether/ligroin

Sources & evidence

ORD record
ord-9f7876abd4244c5da365f1d721883fd3
Source dataset
uspto-grants-1987_06
Patent number
US04675044

Reaction notes

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