Sulfuric acid magnesium salt (1:1) → HCID 178484438, compound

HRID 1968030Notes

Reaction equation

HRID 1968030 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:11].[CH:12]([C:14]1[CH:24]=[CH:23][C:17]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])=[CH:16][CH:15]=1)=O.[O-]S([O-])(=O)=O.[Mg+2]>C(#N)C>[CH3:22][N:20]([CH3:21])[C:18](=[O:19])[C:17]1[CH:23]=[CH:24][C:14](/[CH:12]=[N:1]/[C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][O:5][C:6]3=[O:11])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 105592054-formyl-N,N-dimethylbenzamideHCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 178484438HCID 178484438, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Aminoisobenzofuran-1(3H)-one (2.10 g, 14.1 mmol), 4-formyl-N,N-dimethylbenzamide (2.50 g, 14.1 mmol) and dry MgSO4 (9.84 g, 82 mmol) were added to acetonitrile (170 mL) and stirred under reflux overnight. The mixture was filtered, and the solvent was evaporated under reduced pressure and the residue was re-crystallized to obtain 3.5 g of title compound as a pale solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.01 (s, 3H), 3.15 (s, 3H), 5.43 (s, 2H), 7.38-7.40 (d, J=7.6 Hz, 1H), 7.55-7.61 (m, 3H), 7.80-7.82 (d, J=7.6 Hz, 1H), 7.96-7.98 (d, J=8 Hz, 2H), 8.58 (s, 1H); LC-MS (ESI) m/z: 308 (M+1)+.

Workup

  1. temperatureunder reflux overnight
  2. filtrationThe mixture was filtered
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was re-crystallized

Sources & evidence

ORD record
ord-4aaf2485a6114a3fa0751b767120732c
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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