Triethylamine → 2-(1H-Pyrrol-2-yl)-4H-1,3-benzothiazine-4-one
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas refluxed for 15 hrs
- temperatureAfter cooling
- filtrationthe precipitated crystals were collected by filtration
- 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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