Acetone → HCID 13343851, compound

HRID 365301Notes

Reaction equation

HRID 365301 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=2[CH:3]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].CC(C)=O>>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 80061-Bromo-3-chloropropaneHCID 8200317-hydroxy-2H-1,4-benzothiazin-3(4H)-one

Product 1

HCID 13343851HCID 13343851, compoundYield 50.4%

Procedure

After a mixture consisting of 7-hydroxy-3,4-dihydro-2H-1,4-benzothiazin-3-one (1.812 g, 10 mmol), 1bromo-3-chloropropane (2.362 g, 15 mmol), potassium carbate (4.146 g, 30 mmol) and acetone (40 mmol) was heated under reflux and stirring for 24 hours, insolube matter was filtered off, and the solvent was distilled off under reduced pressure. The residue was subjected to chromatography on a silica gel column (developer: chloroform) to purify the same, and was then recrystallized from acetone. The title compound (1.300 g) was obtained as yellow leaflets (yield: 50.4%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. filtrationinsolube matter was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto purify the same, and
  6. customwas then recrystallized from acetone

Sources & evidence

ORD record
ord-cbbf3a06c7d04efaab9b011975b2bcaf
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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