Sodium Sulfate → 4-(4-(diethoxymethyl)benzylideneamino)isobenzofuran-1(3H)-one

HRID 907804Notes

Reaction equation

HRID 907804 reaction equation
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH3:2].S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH2:26][O:27][C:28]2=[O:33]>ClCCl>[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[N:23][C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH2:26][O:27][C:28]3=[O:33])=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 672585054-(4-(diethoxymethyl)benzylideneamino)isobenzofuran-1(3H)-oneYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-(diethoxymethyl)benzaldehyde (3.75 g, 18 mmol) and anhydrous sodium sulfate (21.3 g, 150 mmol) in anhydrous dichloromethane (300 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 4-(4-(diethoxymethyl)benzylideneamino)isobenzofuran-1(3H)-one (4.3 g, yield 84%) as a light yellow solid. LC-MS (ESI) m/z: 340(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-821b240603c94f6ab122ae6795c3aaf8
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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