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

HRID 748375Notes

Reaction equation

HRID 748375 reaction equation
[C:1]([C:3]1[CH:8]=[N:7][CH:6]=[C:5]([N:9]([CH3:11])[CH3:10])[N:4]=1)#[N:2].[C:12](OC)(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[SH:15].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:10][N:9]([CH3:11])[C:5]1[N:4]=[C:3]([C:1]2[S:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C:12](=[O:20])[N:2]=2)[CH:8]=[N:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 232734596-(Dimethylamino)pyrazine-2-carbonitrile

Product 1

HCID 597501722-[6-(Dimethylamino)-2-pyrazinyl]-4H-1,3-benzothiazine-4-oneYield 32.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Cyano-6-dimethylaminopyrazine (0.50 g, 3.37 mmol) and methyl thiosalicylate (1.14 g, 6.75 mmol) was dissolved in toluene (100 ml), and triethylamine (1.42 ml, 10.1 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 titled compound (0.31 g, 32%) 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-7b3014bd3c3548af84fd1cbd9fa2728d
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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