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

HRID 748372Notes

Reaction equation

HRID 748372 reaction equation
[C:1]([C:3]1[CH:8]=[N:7][CH:6]=[C:5]([S:9][CH3:10])[N:4]=1)#[N:2].[C:11](OC)(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[SH:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:10][S:9][C:5]1[N:4]=[C:3]([C:1]2[S:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[C:11](=[O:19])[N:2]=2)[CH:8]=[N:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 229392812-Cyano-6-methylthiopyrazine

Product 1

HCID 597504732-[6-(Methylthio)-2-pyrazinyl]-4H-1,3-benzothiazine-4-oneYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Cyano-6-methylthiopyrazine (0.80 g, 5.29 mmol) and methyl thiosalicylate (1.34 g, 7.94 mmol) were dissolved in toluene (100 ml), and triethylamine (1.48 ml, 10.6 mmol) was added thereto. The mixture was refluxed for 18 hrs. The solvent was evaporated, and the residue was recrystallized from ethanol to give the tilted compound (0.35 g, 23%) as pale yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 18 hrs
  2. customThe solvent was evaporated
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-eed030ea085f4f70a8149dac85df8f15
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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