Propanal → 5-Ethyl-4-tosyl-2-oxazoline

HRID 908879Notes

Reaction equation

HRID 908879 reaction equation
[S:1]([CH2:11][N:12]=[C:13]=[O:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH:15](=O)[CH2:16][CH3:17].[C-]#N.[Na+].O1CCN=C1>C(O)C>[CH2:16]([CH:17]1[O:14][CH:13]=[N:12][CH:11]1[S:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2])[CH3:15]

Participants

6

Reactant 4

HCID 527PropanalHCID 8929Sodium CyanideHCID 68157OxazolineHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzene

Product 1

HCID 667581855-Ethyl-4-tosyl-2-oxazolineYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of tosylmethylisocyanate (TosMIC, 3.90 g, 20 mmol) and propionaldehyde (1.5 mL 20.4 mmol) in 60 mL dry ethanol, finely powdered sodium cyanide (0.098 g, 2 mmol) was added. The reaction mixture became clear and white crystals of oxazoline began to precipitate in 15 min. The reaction was continuously stirred for an additional 30 min, The mixture was filtered and the crystals were washed with ether-hexane (1:1) before drying. Compound 15 was attained in 81% yield (4.1 g). The structure was confirmed by 1H NMR in CDCl3.

Workup

  1. additionwas added
  2. customto precipitate in 15 min
  3. filtrationThe mixture was filtered
  4. washthe crystals were washed with ether-hexane (1:1)
  5. custombefore drying

Sources & evidence

ORD record
ord-e3c2b9d22abc45629b8bdf211e30996a
Source dataset
uspto-grants-2011_09
Patent number
US08017629B2

Reaction notes

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