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

HRID 1296156Notes

Reaction equation

HRID 1296156 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. LC-MS: [M+1]=254. Purity was >98%.

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-f263f0a5b25548eda98be569f3fe895e
Source dataset
uspto-grants-2007_07
Patent number
US07244739B2

Reaction notes

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