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

HRID 1467650Notes

Reaction equation

HRID 1467650 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-b0d00532303843cb954fc61dcf7a6946
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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