Triethylamine → 2-(1H-Pyrrol-2-yl)-4H-1,3-benzothiazine-4-one

HRID 499267Notes

Reaction equation

HRID 499267 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[NH:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]#[N:18].C(N(CC)CC)C>C1(C)C=CC=CC=1>[NH:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1](=[O:10])[N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 138277Pyrrole-2-carbonitrile

Product 1

HCID 597504242-(1H-Pyrrol-2-yl)-4H-1,3-benzothiazine-4-oneYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (2.00 g, 11.8 mmol), pyrrole-2-carbonitrile (1.10 g, 11.9 mmol), triethylamine (2.00 ml, 14.3 mmol) and toluene (4.0 ml) was refluxed for 15 hrs as described in Example 1. After cooling, the precipitated crystals were collected by filtration and recrystallized from hexane-ethanol to give the titled compound (1.90 g, 73%).

Workup

  1. temperaturewas refluxed for 15 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from hexane-ethanol

Sources & evidence

ORD record
ord-60d27daf1fe24dcda370de0b064998bc
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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