2-Aminothiophenol → 2-(4-Fluorophenyl)-2H-1,4-benzothiazin-3(4H)-one

HRID 5842

Reaction equation

HRID 5842 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C([O-])(=O)C.[Na+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:16](OC)=[O:17]>C(O)C>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH:15]2[C:16](=[O:17])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 517045Sodium AcetateHCID 12717580Methyl 2-bromo-2-(4-fluorophenyl)acetate

Product 1

HCID 136907612-(4-Fluorophenyl)-2H-1,4-benzothiazin-3(4H)-oneYield 87.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-aminothiophenol (12.6 g) and sodium acetate (23.6 g) in ethanol (150 ml) is added methyl α-bromo-4-fluorophenylacetate (23.6 g), and the mixture is stirred at room temperature overnight. After the solvent is distilled off, water is added to the residue. The resulting precipitate is separated by filtration, washed, dried, and then recrystallized from tetrahydrofuran-n-hexane to give 2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine (21.7 g) as crystals. M.p. 216°-219° C.

Workup

  1. distillationAfter the solvent is distilled off
  2. additionwater is added to the residue
  3. customThe resulting precipitate is separated by filtration
  4. washwashed
  5. customdried
  6. customrecrystallized from tetrahydrofuran-n-hexane

Sources & evidence

ORD record
ord-c9f7e092e3be4773aba7a95c56f0342d
Source dataset
uspto-grants-1993_09
Patent number
US05246929

Linked notes

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