3,4-Dichlorobenzaldehyde → HCID 87277538, compound

HRID 2370770Notes

Reaction equation

HRID 2370770 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.[CH3:11][C:12]([S:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])/[CH:5]=[N:17]/[S:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16]

Participants

4

Reactant 2

HCID 227103,4-DichlorobenzaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 87277538HCID 87277538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1-L round-bottomed flask was charged with 3,4-dichlorobenzaldehyde (25.0 g, 143 mmol), 2-methylpropane-2-sulfinamide (17.3 g, 143 mmol), and 200 mL of THF. To this was added Ti(OEt)4 (65.2 g, 286 mmol) over 5 min. The reaction was stirred at rt for 5 h and then poured onto brine. The resulting white precipitate was removed by filtration, and the filter cake was washed with EtOAc. The filtrate was transferred to a separatory funnel and the layers were separated. The organic layers were combined and dried (MgSO4), filtered, and concentrated to give (E)-N-(3,4-dichlorobenzylidene)-2-methylpropane-2-sulfinamide as a white solid.

Workup

  1. additionpoured onto brine
  2. customThe resulting white precipitate was removed by filtration
  3. washthe filter cake was washed with EtOAc
  4. customThe filtrate was transferred to a separatory funnel
  5. customthe layers were separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-74a16dbd51504bf288a9aae4e04e5c31
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

Loading…