Phosphorus sulfide (P2S5) → ethyl 2-[4-(4-bromo-2-fluorophenylmethyl)-3,4-dihydro-3-thioxo-2H-1,4-benzothiazin-2-yl]acetate

HRID 1655897Notes

Reaction equation

HRID 1655897 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][CH:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]2=O)=[C:4]([F:26])[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:28]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][CH:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]2=[S:28])=[C:4]([F:26])[CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 10320899ethyl 2-[4-(4-bromo-2-fluorophenylmethyl)-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetate

Product 1

HCID 54470556ethyl 2-[4-(4-bromo-2-fluorophenylmethyl)-3,4-dihydro-3-thioxo-2H-1,4-benzothiazin-2-yl]acetateYield 110.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4 ml of toluene was added 440 mg of the compound of Example 20 and 310 mg of phosphorus pentasulfide. After the mixture was heated to reflux for 6 hours, the solvent was distilled off. Methylene chloride was added to the mixture, and the insoluble substance was filtered off and the solvent was distilled off. Then the residue was purified by silica gel chromatography to give 350 mg of ethyl 2-[4-(4-bromo-2-fluorophenylmethyl)-3,4-dihydro-3-thioxo-2H-1,4-benzothiazin-2-yl]acetate. The structural formula and physical data of this compound are shown in Table 24.

Workup

  1. temperatureAfter the mixture was heated
  2. temperatureto reflux for 6 hours
  3. distillationthe solvent was distilled off
  4. additionMethylene chloride was added to the mixture
  5. filtrationthe insoluble substance was filtered off
  6. distillationthe solvent was distilled off
  7. customThen the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6d7e804608e84a9783ad46885aa59e23
Source dataset
uspto-grants-1993_10
Patent number
US05252571

Reaction notes

Loading…