Ethylacetamide → N-(4,5-Dimethyl-1,3-oxazol-2-yl)-N-ethylacetamide

HRID 613990Notes

Reaction equation

HRID 613990 reaction equation
[CH2:1]([NH:3][C:4](=[O:6])[CH3:5])[CH3:2].C([Li])CCC.[CH3:12][C:13]1[N:14]=[C:15](S(C)(=O)=O)[O:16][C:17]=1[CH3:18]>C(OCCCC)CCCCC.CCCCCC>[CH2:1]([N:3]([C:15]1[O:16][C:17]([CH3:18])=[C:13]([CH3:12])[N:14]=1)[C:4](=[O:6])[CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 12253EthylacetamideHCID 226270084,5-Dimethyl-2-MethylsulphonyloxazoleHCID 178418339Butyllithium

Product 1

HCID 21323588N-(4,5-Dimethyl-1,3-oxazol-2-yl)-N-ethylacetamide

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 108598Butyl hexyl etherSolvent2×

Procedure

N-Ethyl-acetamide (10.0 g, 0.115 m) in dry butyl hexyl ether (50 ml) was stirred at room temperature under nitrogen during the dropwise addition of a 1.445 M solution of n-butyl lithium in hexane (79.6 ml, 0.115 m). After the addition, the mixture was stirred for 15 minutes and then a solution of 4,5-dimethyl-2-methylsulphonyloxazole (20.0 g, 0.114 m) in dry butyl hexyl ether (50 ml) was added dropwise. The mixture was stirred for 2 hours at room temperature. Isolation of the product and distillation gave a colourless oil, b.p. 61°-62° C/0.3 mm.

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. distillationIsolation of the product and distillation
  4. customgave a colourless oil, b.p. 61°-62° C/0.3 mm

Sources & evidence

ORD record
ord-e8d66543fa40498da2817d495d136e79
Source dataset
uspto-grants-1979_03
Patent number
US04143047

Reaction notes

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