Pyridine → 10H-phenothiazine-2-carbothioamide

HRID 237345Notes

Reaction equation

HRID 237345 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 reagent in solution in 40 ml of 1,4-dioxane to which 20 ml of pyridine has been added is heated at 110° C. for 1 h 30. 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 decantation, 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 extracted with acetone. The acetone filtrate is then concentrated under vacuum and the evaporation residue is then purified using a silica column (eluent: Heptane/AcOEt:1/1 to 416). 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. washdecantation, the organic phase is washed successively with 100 ml of a 1N aqueous solution of HCl and 100 ml of salt water
  4. dry with materialAfter drying over sodium sulphate, filtration and evaporation of the solvent under vacuum
  5. customan orange powder is obtained
  6. washThis powder is washed with Et2O
  7. extractionextracted with acetone
  8. concentrationThe acetone filtrate is then concentrated under vacuum
  9. customthe evaporation residue is then purified

Sources & evidence

ORD record
ord-3396506667f6480ca658f568cdd5805c
Source dataset
uspto-grants-2014_02
Patent number
US08642591B2

Reaction notes

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