Iodoethane → N,2-Diethyl-N-(4-methyl-1,3-oxazol-2-yl)butanamide

HRID 26484Notes

Reaction equation

HRID 26484 reaction equation
[H-].[Na+].[CH2:3]([CH:5]([CH2:15][CH3:16])[C:6]([NH:8][C:9]1[O:10][CH:11]=[C:12]([CH3:14])[N:13]=1)=[O:7])[CH3:4].[CH2:17](I)[CH3:18]>CN(C)C=O>[CH2:17]([N:8]([C:9]1[O:10][CH:11]=[C:12]([CH3:14])[N:13]=1)[C:6](=[O:7])[CH:5]([CH2:3][CH3:4])[CH2:15][CH3:16])[CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12556852HCID 12556852, compound

Product 1

HCID 21323622N,2-Diethyl-N-(4-methyl-1,3-oxazol-2-yl)butanamideYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (2.8 g. of a 50% dispersion in oil, 0.058 mol) was added in small portions to a stirred solution of 2-(2-ethylbutyramido)-4-methyloxazole (8.0 g., 0.041 mol) in dimethylformamide (100 ml.) at -5° to 0° C. The mixture was stirred for 2 hours at room temperature and then ethyl iodide (4.7 ml. 0.058 mol) was added. The mixture was stirred for a further 2 hours at room temperature and then poured onto ice-water (250 ml.) and extracted with ether (3 × 100 ml.). The extract was washed with dilute hydrochloric acid, then with sodium chloride solution, dried over sodium sulphate and evaporated. The residue was distilled under vacuum to give the product 4.7 g. (51%) b.p. 71-72° C/0.3 mm.

Workup

  1. stirringThe mixture was stirred for a further 2 hours at room temperature
  2. additionpoured onto ice-water (250 ml.)
  3. extractionextracted with ether (3 × 100 ml.)
  4. washThe extract was washed with dilute hydrochloric acid
  5. dry with materialwith sodium chloride solution, dried over sodium sulphate
  6. customevaporated
  7. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-07097c77bf794604bc3b2c694c5a8945
Source dataset
uspto-grants-1979_04
Patent number
US04150143

Reaction notes

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