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

HRID 907975Notes

Reaction equation

HRID 907975 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].S([O-])([O-])(=O)=O.[Mg+2].[NH2:19][C:20]1[CH:28]=[C:27]([F:29])[CH:26]=[C:25]2[C:21]=1[CH2:22][O:23][C:24]2=[O:30]>C(#N)C>[CH3:1][N:2]([CH2:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[N:19]/[C:20]2[CH:28]=[C:27]([F:29])[CH:26]=[C:25]3[C:21]=2[CH2:22][O:23][C:24]3=[O:30])=[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 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 4-((dimethylamino)methyl)benzaldehyde (4 g, 24.5 mmol) and anhydrous magnesium sulfate (15.8 g, 111.5 mmol) in anhydrous acetonitrile (100 mL) was added 4-amino-6-fluoroisobenzofuran-1(3H)-one (4 g, 22.3 mmol) at 0° C. After the addition, the mixture was stirred at reflux for 3 days. The mixture was filtered and the cake was washed with ethyl acetate (50 mL×3). The filtrate was concentrated to give crude product, which was re-crystallized with isopropanol to give the title compound (3.7 g, yield 55%). LC-MS (ESI) m/z: 314 (M+1)+.

Workup

  1. additionAfter the addition
  2. temperatureat reflux for 3 days
  3. filtrationThe mixture was filtered
  4. washthe cake was washed with ethyl acetate (50 mL×3)
  5. concentrationThe filtrate was concentrated
  6. customto give crude product, which
  7. customwas re-crystallized with isopropanol

Sources & evidence

ORD record
ord-b3b3d26ba6ac43408ed352fa00f04835
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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