Sulfuric acid magnesium salt (1:1) → HCID 178480587, compound

HRID 1968128Notes

Reaction equation

HRID 1968128 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]=[C:17]([F:19])[CH:16]=[C:15]2[C:11]=1[CH2:12][O:13][C:14]2=[O:20].S([O-])([O-])(=O)=O.[Mg+2]>C(#N)C>[F:19][C:17]1[CH:16]=[C:15]2[C:11]([CH2:12][O:13][C:14]2=[O:20])=[C:10](/[N:9]=[CH:7]/[C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 672589744-Amino-6-fluoroisobenzofuran-1(3H)-one

Product 1

HCID 178480587HCID 178480587, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-methyl-1H-imidazole-2-carbaldehyde (659 mg, 6.0 mmol), 4-amino-6-fluoroisobenzofuran-1(3H)-one (1.0 g, 6.0 mmol), and anhydrous magnesium sulfate (7.2 g, 60.0 mmol) in acetonitrile (100 mL) was heated to reflux for 2 days. The solution was filtered and the solvents were removed in vacuum. The crude product was re-crystallized from isopropanol to afford the title compound (1.068 g, yield 68%) LC-MS (ESI) m/z: 260 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 4.04 (s, 3H), 5.49 (s, 2H), 7.24 (s, 1H), 7.54-7.58 (m, 2H), 7.73-7.76 (m, 1H), 8.70 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-d1296a26075b40388cac418d8521cfc6
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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