Phosphorus sulfide (P2S5) → HCID 14234715, compound

HRID 622367Notes

Reaction equation

HRID 622367 reaction equation
[CH:1]([CH:4]1[C:9](=O)[N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[S:5]1)([CH3:3])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>C1(C)C=CC=CC=1>[CH:1]([CH:4]1[C:9](=[S:21])[N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[S:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 14257332HCID 14257332, compound

Product 1

HCID 14234715HCID 14234715, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 3,4-dihydro-2-isopropyl-3-oxo-2H1,4-benzothiazine-4-acetate (50.0 g), phosphorus pentasulfide (79.5 g), and toluene (450 ml) was refluxed for 5.5 hours with stirring. After cooling, the insoluble matter was removed by filtration, and the solvent was evaporated off. To the residue isopropyl ether (300 ml) was added, and the insoluble matter was removed by filtration. The filtrate was concentrated, and the residue was crystallized from 2-propanol, to give methyl 3,4-dihydro-2- isopropyl-3-thioxo-2H-1,4-benzothiazine-4-acetate as crystals. Yield was 27.0 g (51.0%). Recrystallization from 2-propanol gave yellow prisms. mp 99°-100° C.

Workup

  1. temperaturewas refluxed for 5.5 hours
  2. temperatureAfter cooling
  3. customthe insoluble matter was removed by filtration
  4. customthe solvent was evaporated off
  5. additionTo the residue isopropyl ether (300 ml) was added
  6. customthe insoluble matter was removed by filtration
  7. concentrationThe filtrate was concentrated
  8. customthe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-50de3e9b9f7c4773b622f1e6ab7fb2d6
Source dataset
uspto-grants-1988_09
Patent number
US04771050

Reaction notes

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