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

HRID 748468Notes

Reaction equation

HRID 748468 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-003c007f5f964755b44f7d33fa7b77eb
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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