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

HRID 1968111Notes

Reaction equation

HRID 1968111 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-a7b3030b42a34aab9df2e31206d651ff
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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