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

HRID 1583053Notes

Reaction equation

HRID 1583053 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

K2CO3 (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 solvent was removed in vacuum. 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. customthe solvent was removed in vacuum
  3. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-e800f9a0402149b9be57132186002671
Source dataset
uspto-grants-2004_05
Patent number
US06740649B2

Reaction notes

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