Triethylamine → 2-(5,6,7,8-Tetrahydro-2-quinolyl)-4H-1,3-benzothiazine-4-one

HRID 748209Notes

Reaction equation

HRID 748209 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[C:12]([C:14]1[CH:23]=[CH:22][C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:15]1[C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=2[CH:22]=[CH:23][C:14]=1[C:12]1[S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1](=[O:10])[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 114464875,6,7,8-Tetrahydroquinoline-2-carbonitrile

Product 1

HCID 597503672-(5,6,7,8-Tetrahydro-2-quinolyl)-4H-1,3-benzothiazine-4-oneYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (0.43 g, 2.5 mmol), 2-cyano-5,6,7,8-tetrahydroquinoline (0.40 g, 2.5 mmol), triethylamine (0.50 ml, 3.8 mmol) and toluene (2.0 ml) was refluxed for 17 hrs. After cooling, the precipitated crystals were collected by filtration and recrystallized from ethanol to give the titled compound (0.22 g, 30%)

Workup

  1. temperaturewas refluxed for 17 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0d06458d9e644ba9962971f79bd199f9
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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