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

HRID 2181073Notes

Reaction equation

HRID 2181073 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 (0.69 mL, 8.0 mmol) were added to a solution of 2-aminothiophenol (1.0 g, 8.0 mmol) in 20 mL of acetone at room temperature. The reaction mixture was stirred overnight. The insoluble material was filtered off and the solvent was removed under reduced pressure. 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 under reduced pressure
  3. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-cc4a33992b1846e687b8eea052032b1e
Source dataset
uspto-grants-2005_05
Patent number
US06890915B2

Reaction notes

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