Ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate → Ethyl 2-[4-(5,7-difluorobenzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetate

HRID 1655895Notes

Reaction equation

HRID 1655895 reaction equation
[C:1]([CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]1=[O:20])#[N:2].Cl.N[C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[C:24]=1[SH:31]>C(O)C>[F:29][C:27]1[CH:26]=[C:25]([F:30])[C:24]2[S:31][C:1]([CH2:3][N:4]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[S:7][CH:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]3=[O:20])=[N:2][C:23]=2[CH:28]=1

Participants

4

Reactant 2

HCID 10062806Ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetateHCID 197896412-Amino-4,6-difluorothiophenol hydrochloride

Product 1

HCID 10025918Ethyl 2-[4-(5,7-difluorobenzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetateYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate (580 mg) and 474 mg of 2-amino-4,6-difluorothiophenol hydrochloride were added to 4 ml of anhydrous ethanol, the mixture was heated to reflux under argon atmosphere. After 15 hours, the solvent was distilled off. Water was added to the mixture, and extracted with ethyl acetate. After the drying of the organic layer over anhydrous magnesium sulfate, the solvent was distilled off. The resulting oily matter was subjected to alumina column chromatography. Elution with hexane-ehtyl acetate gave 660 mg of the title compound. The structural formula and physical data of this compound are shown in Table 19.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under argon atmosphere
  3. distillationthe solvent was distilled off
  4. additionWater was added to the mixture
  5. extractionextracted with ethyl acetate
  6. dry with materialAfter the drying of the organic layer over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. washElution with hexane-ehtyl acetate

Sources & evidence

ORD record
ord-a295049dbe98494986e41762927628fc
Source dataset
uspto-grants-1993_10
Patent number
US05252571

Reaction notes

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