Sulfuric acid magnesium salt (1:1) → HCID 178483209, compound

HRID 907982Notes

Reaction equation

HRID 907982 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH3:3].[NH2:13][C:14]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]2[C:15]=1[CH2:16][O:17][C:18]2=[O:24].S([O-])([O-])(=O)=O.[Mg+2]>C(#N)C>[CH3:1][N:2]([CH2:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[N:13]/[C:14]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]3[C:15]=2[CH2:16][O:17][C:18]3=[O:24])=[CH:7][CH:6]=1)[CH3:3]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 1932514-DimethylaminomethylbenzaldehydeHCID 672589744-Amino-6-fluoroisobenzofuran-1(3H)-one

Product 1

HCID 178483209HCID 178483209, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-((dimethylamino)methyl)benzaldehyde (1.0 g, 6.13 mmol), 4-amino-6-fluoroisobenzofuran-1(3H)-one (1.024 g, 6.13 mmol) and anhydrous magnesium sulfate (7.356 g, 61.3 mmol) in acetonitrile (50 ml) was heated at reflux for 2 days. The solution was filtered and concentrated in vacuum. The crude product was re-crystallized with isopropanol to obtain the title compound (1.15 g, yield 60%). LC-MS (ESI) m/z: 313 (M+1)+. 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.28 (s, 6H), 3.52 (s, 2H), 5.38-5.38 (m, 2H), 7.09-7.12 (m, 1H), 7.42-7.44 (m, 1H), 7.46-7.48 (d, J=8 Hz, 2H), 7.87-7.89 (d, J=8 Hz, 2H), 8.51 (s, 1H).

Workup

  1. temperatureat reflux for 2 days
  2. filtrationThe solution was filtered
  3. concentrationconcentrated in vacuum
  4. customThe crude product was re-crystallized with isopropanol

Sources & evidence

ORD record
ord-070d7e7f381a4b18bcd399c482575c5e
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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