Triethylamine → 2-[6-(3-Phenylpropyl)thio-2-pyridyl]-4H-1,3-benzothiazine-4-one

HRID 499414Notes

Reaction equation

HRID 499414 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:4]=1)#[N:2].[C:19](OC)(=[O:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[SH:22].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:13]1([CH2:12][CH2:11][CH2:10][S:9][C:5]2[N:4]=[C:3]([C:1]3[S:22][C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[C:19](=[O:27])[N:2]=3)[CH:8]=[CH:7][CH:6]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 229393782-Cyano-6-(3-phenylpropylthio)pyridine

Product 1

HCID 597504222-[6-(3-Phenylpropyl)thio-2-pyridyl]-4H-1,3-benzothiazine-4-oneYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Cyano-6-(3-phenylpropylthio)pyridine (1.84 g, 7.22 mmol) and methyl thiosalicylate (1.21 g, 7.22 mmol) were dissolved in toluene (30 ml), and triethylamine (1.52 ml, 10.8 mmol) was added thereto. The reaction mixture was refluxed for 48 hrs. The solvent was evaporated and the residue was recrystallized from ethanol to give the titled compound (1.06 g, 38%) as pale yellow crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. customThe solvent was evaporated
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-01420aff76564b7084312aebdf1e920e
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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