Benzaldehyde → HCID 178519071, compound

HRID 1467578Notes

Reaction equation

HRID 1467578 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].[NH2:15][C:16]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]2[C:17]=1[CH2:18][O:19][C:20]2=[O:26]>C(#N)C>[CH:1](=[N:15]/[C:16]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]2[C:17]=1[CH2:18][O:19][C:20]2=[O:26])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 672589744-Amino-6-fluoroisobenzofuran-1(3H)-one

Product 1

HCID 178519071HCID 178519071, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of benzaldehyde (4.125 g, 29.9 mmol) and anhydrous magnesium sulfate (36 g, 299 mmol) in anhydrous acetonitrile (200 mL) was added 4-amino-6-fluoroisobenzofuran-1(3H)-one (5 g, 29.9 mmol) at 0° C. After the addition, the mixture was stirred at room temperature for 6 days. The mixture was filtered and the cake was washed with ethyl acetate (50 mL×3). The filtrate was concentrated to give crude product. The crude product was washed with petroleum ether to give (E)-4-(benzylideneamino)-6-fluoroisobenzofuran-1(3H)-one (5 g, yield: 66%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 5.40 (s, 2); 7.11-7.14 (dd, 1H), 7.44-7.46 (dd, 2H), 7.53-7.59 (m, 3H), 7.93-7.95 (m, 2H), 8.54 (s, 1H); LC-MS (ESI) m/z: 256 (M+1)+.

Workup

  1. additionAfter the addition
  2. filtrationThe mixture was filtered
  3. washthe cake was washed with ethyl acetate (50 mL×3)
  4. concentrationThe filtrate was concentrated
  5. customto give crude product
  6. washThe crude product was washed with petroleum ether

Sources & evidence

ORD record
ord-5e8e43a3c6a442b1af6915cc63926d6e
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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