Pyridine → 10H-phenothiazine-2-carbothioamide

HRID 352332Notes

Reaction equation

HRID 352332 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15]([NH2:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1.N1C=CC=CC=1>O1CCOCC1>[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15](=[S:27])[NH2:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 87949Lawesson's reagentHCID 2271157510H-phenothiazine-2-carboxamide

Product 1

HCID 2271158710H-phenothiazine-2-carbothioamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A reaction mixture comprising 3.4 g (14 mmoles) of 10H-phenothiazine-2-carboxamide (J. Org. Chem. (1961) 26, 1138-1143) and 3.4 g (8.4 mmoles) of Lawesson's reagent in solution in 40 ml of 1,4-dioxane to which 20 ml of pyridine is added is heated at 110° C. for 1 hour 30 minutes. The brown solution is then concentrated under vacuum and the residue is diluted in 200 ml of AcOEt and 100 ml of H2O. After stirring and decanting, the organic phase is washed successively with 100 ml of a 1N aqueous solution of HCl and 100 ml of salt water. After drying over sodium sulphate, filtration and evaporation of the solvent under vacuum, an orange powder is obtained. This powder is washed with Et2O, the filtrate is eliminated, and extraction is carried out with acetone. The acetonic filtrate is then concentrated under vacuum and the evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 1/1 to 4/6). Orange powder. Melting point: 208-209° C.

Workup

  1. concentrationThe brown solution is then concentrated under vacuum
  2. additionthe residue is diluted in 200 ml of AcOEt
  3. customdecanting
  4. washthe organic phase is washed successively with 100 ml of a 1N aqueous solution of HCl and 100 ml of salt water
  5. dry with materialAfter drying over sodium sulphate, filtration and evaporation of the solvent under vacuum
  6. customan orange powder is obtained
  7. washThis powder is washed with Et2O
  8. extractionextraction
  9. concentrationThe acetonic filtrate is then concentrated under vacuum
  10. customthe evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 1/1 to 4/6)

Sources & evidence

ORD record
ord-07c578534b594b7e862cc8e8d5ca22c3
Source dataset
uspto-grants-2004_06
Patent number
US06747024B1

Reaction notes

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