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

HRID 499648Notes

Reaction equation

HRID 499648 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]#[N:8])[N:6]=1.[C:9](OC)(=[O:17])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[SH:12].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9](=[O:17])[N:8]=2)[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 27992812-Methyl-1,3-thiazole-4-carbonitrile

Product 1

HCID 597502152-(2-Methyl-1,3-thiazol-4-yl)-4H-1,3-benzothiazin-4-oneYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Methyl-1,3-thiazole-4-carbonitrile (0.46 g, 3.7 mmol) and methyl thiosalicylate (1.26 g, 7.4 mmol) were dissolved in toluene (6 ml), and triethylamine (3.0 ml, 21.5 mmol) was added thereto. The mixture was refluxed for 15 hrs. After cooling, the precipitates were collected by filtration and recrystallized from ethanol to give the titled compound (0.75 g, 78%) as white crystals.

Workup

  1. temperatureThe mixture was refluxed for 15 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitates were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4b4a577c76b24c8280ca8df4f843aaca
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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