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

HRID 1593333Notes

Reaction equation

HRID 1593333 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-7d65311fd1ec401e9ce69bda58127296
Source dataset
uspto-grants-2007_11
Patent number
US07294624B2

Reaction notes

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