Triethylamine → 2-(1,3-thiazol-2-yl)-4H-1,3-benzothiazin-4-one

HRID 748469Notes

Reaction equation

HRID 748469 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]#[N:7].[C:8](OC)(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[SH:11].C(N(CC)CC)C>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8](=[O:16])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 151114801,3-Thiazole-2-carbonitrile

Product 1

HCID 597503412-(1,3-thiazol-2-yl)-4H-1,3-benzothiazin-4-oneYield 71.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,3-Thiazole-2-carbonitrile (0.32 g, 2.9 mmol) and methyl thiosalicylate (0.98 g, 5.8 mmol) were dissolved in toluene (4 ml), and triethylamine (2.0 ml, 14.3 mmol) was added thereto. The reaction mixture was refluxed for 2 hrs. After cooling, the precipitates were collected by filtration and recrystallized from diisopropyl ether-ethanol to give the titled compound (0.51 g, 70%) as yellow crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitates were collected by filtration
  4. customrecrystallized from diisopropyl ether-ethanol

Sources & evidence

ORD record
ord-1a9e12e4546f4710b7ed182e904ca15e
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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