Triethylamine → 2-[[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]-1H-isoindole-1,3(2H)-dione

HRID 499508Notes

Reaction equation

HRID 499508 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[N:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][CH:14]=1.[C:21](OC)(=[O:29])[C:22]1[C:23](=[CH:25][CH:26]=[CH:27][CH:28]=1)[SH:24].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:29]=[C:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[S:24][C:19]([C:17]2[N:18]=[C:13]([CH2:12][N:3]3[C:2](=[O:1])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[C:4]3=[O:11])[CH:14]=[CH:15][CH:16]=2)=[N:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 100383916-Phthalimidomethyl-2-pyridinecarbonitrile

Product 1

HCID 597501872-[[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]-1H-isoindole-1,3(2H)-dioneYield 78.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-pyridinecarbonitrile (1.25 g, 4.7 mmol) and methyl thiosalicylate (1.59 g, 9.4 mmol) were dissolved in toluene (10 ml), and triethylamine (5.0 ml, 35.8 mmol) was added thereto. The reaction mixture was refluxed for 15 hrs. After cooling, the precipitates were collected by filtration and recrystallized from hexane-chloroform to give the titled compound (1.48 g, 78%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitates were collected by filtration
  4. customrecrystallized from hexane-chloroform

Sources & evidence

ORD record
ord-9f823fe2ea55403badbef9bd469ac40a
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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