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

HRID 499392Notes

Reaction equation

HRID 499392 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-e9acdc91ff094a74be4e747ef2caa135
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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