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

HRID 1715718Notes

Reaction equation

HRID 1715718 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].[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 68157OxazolineHCID 5360545SodiumHCID 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 cyamide (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-54f1d5469bf04b658bb37648afaf8952
Source dataset
uspto-grants-2010_09
Patent number
US07799808B2

Reaction notes

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