Sulfuric acid magnesium salt (1:1) → HCID 178519077, compound

HRID 1467581Notes

Reaction equation

HRID 1467581 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:12].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[F:11][C:9]1[CH:8]=[C:7]2[C:3]([CH2:4][O:5][C:6]2=[O:12])=[C:2](/[N:1]=[CH:18]/[C:17]2[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 680234-FluorobenzaldehydeHCID 672589744-Amino-6-fluoroisobenzofuran-1(3H)-one

Product 1

HCID 178519077HCID 178519077, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-amino-6-fluoroisobenzofuran-1(3H)-one (1.5 g, 8.98 mmol), 4-fluorobenzaldehyde (1.67 g, 13.47 mmol) and 12.75 g of MgSO4 were added into 40 ml of DCM and stirred under reflux overnight, then the mixture was evaporated under reduced pressure and the residues was dried in vacuum. 850 mg of (E)-6-fluoro-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one was obtained. 1H-NMR (400 MHz, CDCl3) δ (ppm): 5.37 (s, 2); 7.09-7.12 (dd, 1H), 7.19-7.23 (t, 2H), 7.43-7.45 (dd, 1H), 7.92-7.95 (m, 2H), 8.49 (s, 1H); LC-MS (ESI) m/z: 274 (M+1)+.

Workup

  1. temperatureunder reflux overnight
  2. customthe mixture was evaporated under reduced pressure
  3. customthe residues was dried in vacuum

Sources & evidence

ORD record
ord-9acbaac26dd04904b1987b4367991f26
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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