Sulfuric acid magnesium salt (1:1) → HCID 178484454, compound

HRID 907923Notes

Reaction equation

HRID 907923 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:10]([CH:13]=O)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[NH2:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][O:19][C:20]2=[O:25].S([O-])([O-])(=O)=O.[Mg+2]>C(#N)C>[F:1][C:2]1[CH:12]=[CH:11][C:10](/[CH:13]=[N:15]/[C:16]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:17]=2[CH2:18][O:19][C:20]3=[O:25])=[CH:9][C:3]=1[C:4]([N:6]([CH3:7])[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-oneHCID 83383404HCID 83383404, compound

Product 1

HCID 178484454HCID 178484454, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-fluoro-5-formyl-N,N-dimethylbenzamide (2.38 g, 12.2 mmol), 4-aminoisobenzofuran-1(3H)-one (1.82 g, 12.2 mmol), anhydrous magnesium sulfate (14.67 g, 122 mmol) in acetonitrile (100 ml) was heated to reflux for 2 days. The solution was filtered and removed in vacuum. The crude product was re-crystal with isopropanol to give the title compound (1.5 g, yield: 37%) 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.91-2.92 (d, J=0.4 Hz, 3H), 3.07 (s, 3H), 5.55 (s, 2H), 7.52-7.56 (t, J=8.8 Hz, 1H), 7.67-7.70 (m, 2H), 7.76-7.78 (m, 1H), 8.02-8.04 (m, 1H), 8.10-8.14 (m, 1H), 8.83 (s, 1H); LC-MS (ESI) m/z: 327 (M+1)+.

Workup

  1. temperatureto reflux for 2 days
  2. filtrationThe solution was filtered
  3. customremoved in vacuum

Sources & evidence

ORD record
ord-f0585f926f474c74b21237f9af247df7
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

Loading…