Toluene → HCID 9972693, compound

HRID 275276Notes

Reaction equation

HRID 275276 reaction equation
[N:1]1[C:6]2[S:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=O)[NH:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.[C:22]1([CH3:28])C=CC=CC=1>CN(C)C1C=CC=CC=1>[CH3:2][N:1]1[CH2:28][CH2:22][N:11]([C:10]2[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[S:7][C:6]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[N:11]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 3243778HCID 3243778, compound

Product 1

HCID 9972693HCID 9972693, compound

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineCatalyst

Procedure

3 g 5H, 6H-pyrido(2,3-b)benzo-1,4-thiazepine-6-one are refluxed with an excess of phosphorous oxychloride and 5 drops of N,N-dimethylaniline for 20 hours. The solution is taken up with anhydrous toluene and evaporated to dryness. The residue is taken up with 5 ml anhydrous toluene and an excess of N-methylpiperazine is added. This mixture is then refluxed for 2-4 hours. Once the reaction is terminated, the solvent is eliminated. The colored mass is taken up with chloroform and washed two times with water. The chloroformic phase is decolored with carbon and dried. After concentration into a small volume, the mixture is passed through a silica column (Woelm act III). The eluent phase is acetone. Once separated, the different phases containing the above mentioned product are evaporated to dryness. The residue is recrystallized in petrolein 100/140. The melting point is 134° C.

Workup

  1. customevaporated to dryness
  2. additionan excess of N-methylpiperazine is added
  3. temperatureThis mixture is then refluxed for 2-4 hours
  4. customOnce the reaction is terminated
  5. washwashed two times with water
  6. customdried
  7. concentrationAfter concentration into a small volume
  8. customOnce separated
  9. additionthe different phases containing the
  10. customare evaporated to dryness
  11. customThe residue is recrystallized in petrolein 100/140

Sources & evidence

ORD record
ord-93b35e3ca60245cd806511cbfbf16572
Source dataset
uspto-grants-1995_02
Patent number
US05393752

Reaction notes

Loading…