Benzaldehyde → HCID 178519069, compound

HRID 1967930Notes

Reaction equation

HRID 1967930 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][O:20][C:21]2=[O:26]>ClCCl>[CH:1](=[N:16]/[C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][O:20][C:21]2=[O:26])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24436Sodium SulfateHCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 178519069HCID 178519069, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of benzaldehyde (1.91 g, 18 mmol) and anhydrous sodium sulfate (21.3 g, 150 mmol) in anhydrous dichloromethane (100 mL) was added 4-aminoisobenzofuran-1(3H)-one (2.24 g, 15 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 dichloromethane (50 mL×3). The filtrate was concentrated to give crude product. The crude product was washed with petroleum ether to give (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (3.38 g, yield 95%) as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 5.41 (s, 2H), 7.36-7.37 (d, J=7.6 Hz, 1H), 7.49-7.59 (m, 4H), 7.77-7.78 (d, J=7.6 Hz, 1H), 7.92-7.94 (d, J=8.0 Hz, 2H), 8.55 (s, 1H), LC-MS (ESI) m/z: 238 (M+1)+.

Workup

  1. additionAfter the addition
  2. filtrationThe mixture was filtered
  3. washthe cake was washed with dichloromethane (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-ce0246f985974b6288284f9ea22144f5
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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