1,2-Dibromoethane → 2,3-Dihydro-1,4-benzothiazine

HRID 736678Notes

Reaction equation

HRID 736678 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9]Br.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[SH:18]>CC(C)=O>[S:18]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 87132-AminothiophenolHCID 11430Potassium Carbonate

Product 1

HCID 1510642,3-Dihydro-1,4-benzothiazineYield 66.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (4.4 g, 31.9 mmol) and 1,2-dibromoethane (690 μL, 8.0 mmol) were added to a solution of 2-aminothiophenol (1.0 g, 8.0 mmol) in 20 mL of acetone at rt. The reaction mixture was stirred overnight. The insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was purified on silica gel column to provide 3,4-dihydro-2H-1,4-benzothiazine (0.8 g, 66%). MS (ES+): 152 (M+1).

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-fab4da57d8404b518fd876fd3537f6c3
Source dataset
uspto-grants-2009_09
Patent number
US07595317B2

Reaction notes

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