p-Toluenesulfonic acid → 3,4-Dihydro-2H,6H-[1,3]thiazino[3,2-b]isoquinolin-6-one

HRID 261086Notes

Reaction equation

HRID 261086 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[CH2:7][C:6]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1Cl>[O:11]=[C:10]1[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[CH:7]=[C:6]2[S:1][CH2:2][CH2:3][CH2:4][N:5]12

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 12593121HCID 12593121, compound

Product 1

HCID 1718613,4-Dihydro-2H,6H-[1,3]thiazino[3,2-b]isoquinolin-6-one

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 112 mg. of N-(3-mercaptopropyl)homophthalimide, 172 mg. of p-toluenesulfonic acid, and 4 ml. of o-dichlorobenzene was heated to 120° C. for 30 minutes. After cooling the reaction mixture, the solvent was distilled off from the reaction mixture under reduced pressure and the residue obtained was extracted with 50 ml. of benzene. The extract was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. By recrystallizing the residue thus obtained from isopropyl alcohol, 70 mg. of 6-oxo-3,4-dihydro-2H,6H-1,3-thiazino[3,2-b]isoquinoline was obtained.

Workup

  1. additionA mixture of 112 mg
  2. temperatureAfter cooling the reaction mixture
  3. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  4. customthe residue obtained
  5. extractionwas extracted with 50 ml
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customBy recrystallizing the residue
  10. customthus obtained from isopropyl alcohol, 70 mg

Sources & evidence

ORD record
ord-dbe1b8399d1641448a137de4e7874155
Source dataset
uspto-grants-1979_08
Patent number
US04163844

Reaction notes

Loading…