Sulfuric acid magnesium salt (1:1) → HCID 178480586, compound

HRID 907993Notes

Reaction equation

HRID 907993 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[NH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][O:13][C:14]2=[O:19].S([O-])([O-])(=O)=O.[Mg+2]>C(#N)C>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1/[CH:7]=[N:9]/[C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][O:13][C:14]2=[O:19]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 178480586HCID 178480586, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-methyl-1H-imidazole-2-carbaldehyde (680 mg, 6.18 mmol), 4-aminoisobenzofuran-1(3H)-one (920.8 mg, 6.18 mmol) and anhydrous magnesium sulfate (7.41 g, 61.8 mmol) in acetonitrile (100 ml) was heated to reflux for two days. The mixture was filtered and the solvents were removed in vacuum. The crude product was re-crystallized from isopropanol to get the title compound (1.49 g, yield 68%). LC-MS (ESI) m/z: 242 (M+1)+. 1H-NMR (400 MHz, DMSO-d6); 4.06 (s, 3H), 5.52 (s, 2H), 7.22 (s, 1H), 7.52 (s, 1H), 7.65-7.67 (m, 1H), 7.72-7.74 (m, 2H), 8.66 (s, 1H).

Workup

  1. temperatureto reflux for two days
  2. filtrationThe mixture was filtered
  3. customthe solvents were removed in vacuum
  4. customThe crude product was re-crystallized from isopropanol

Sources & evidence

ORD record
ord-fa34d9168162443780fb10b39a777f30
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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