Phosphorus sulfide (P2S5) → Ethyl 2-[4-(5-fluorobenzothiazol-2-yl)methyl-3,4-dihydro-3-thioxo-2H-1,4-benzothiazin-2-yl]acetate

HRID 1655896Notes

Reaction equation

HRID 1655896 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[S:14][CH:13]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]3=O)=[N:7][C:6]=2[CH:28]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:30]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[S:14][CH:13]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]3=[S:30])=[N:7][C:6]=2[CH:28]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 9909828Ethyl 2-[4-(5-fluorobenzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetate

Product 1

HCID 10320610Ethyl 2-[4-(5-fluorobenzothiazol-2-yl)methyl-3,4-dihydro-3-thioxo-2H-1,4-benzothiazin-2-yl]acetateYield 71.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 10 ml of toluene were added 720 mg of the compound of Example 1 and 770 mg of phosphorus pentasulfide. The mixture was heated to reflux for 4 hours. After the mixture has been cooled, the insoluble substance was filtered off and the solvent was distilled off. The residue was purified by silica gel chromatography to give 535 mg of the title compound. The structural formula and physical data of this compound are shown in Table 23.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter the mixture has been cooled
  4. filtrationthe insoluble substance was filtered off
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bf57a48b69b34098ac87c74b1cc58048
Source dataset
uspto-grants-1993_10
Patent number
US05252571

Reaction notes

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