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

HRID 748196Notes

Reaction equation

HRID 748196 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([S:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:21]([S:20][C:16]1[N:15]=[C:14]([C:12]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:13]=2)[CH:19]=[CH:18][CH:17]=1)[CH2:22][CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 229393372-Cyano-6-isopentylthiopyridine

Product 1

HCID 229395222-[6-(Isoamylthio)-2-pyridyl]-4H-1,3-benzothiazine-4-oneYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (1.21 g, 7.2 mmol), 2-cyano-6-isopentylthiopyridine (1.48 g, 7.2 mmol), triethylamine (1.5 ml, 10.8 mmol) and toluene (30 ml) was refluxed for 48 hrs. The reaction mixture was concentrated under reduced pressure to give the precipitated crystals, which were recrystallized from ethyl acetate-hexane to give the titled compound (0.64 g, 26%).

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give the precipitated crystals, which
  4. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ccde31d0517c443ba5f5babb161013ae
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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