Sulfuric acid magnesium salt (1:1) → HCID 178463922, compound

HRID 908007Notes

Reaction equation

HRID 908007 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].S([O-])([O-])(=O)=O.[Mg+2].[NH2:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH2:24][O:25][C:26]2=[O:31]>C(#N)C>[CH2:1]([N:3]([CH2:6][C:7]1[CH:14]=[CH:13][C:10](/[CH:11]=[N:21]/[C:22]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:23]=2[CH2:24][O:25][C:26]3=[O:31])=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-oneHCID 13023000HCID 13023000, compound

Product 1

HCID 178463922HCID 178463922, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 4-((diethylamino)methyl)benzaldehyde (3.7 g, 19.4 mmol) and anhydrous magnesium sulfate (11.6 g, 96.8 mmol) in anhydrous acetonitrile (100 mL) was added 4-aminoisobenzofuran-1(3H)-one (2.89 g, 19.4 mmol) at 0° C. After the addition the mixture was stirred refluxed 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 from isopropanol to give the title compound (2.1 g, yield: 32%). LC-MS (ESI) m/z: 323 (M+1)+.

Workup

  1. additionAfter the addition the mixture
  2. temperaturerefluxed 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 from isopropanol

Sources & evidence

ORD record
ord-2bded5e41d804b829eccd10e08903b6c
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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