Acetyl chloride → 5-Formylaminomethyl-3-methylisoxazole

HRID 1196858Notes

Reaction equation

HRID 1196858 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=O.C[O-].[Na+].[Na].C(Cl)(=O)C.[CH:14]([NH:16][CH2:17][C:18]#[CH:19])=[O:15]>CN(C)C(=O)C.CO>[CH:14]([NH:16][CH2:17][C:18]1[O:3][N:1]=[C:4]([CH3:5])[CH:19]=1)=[O:15]

Participants

8

Reactant 5

HCID 6367Acetyl chlorideHCID 6587NitroethaneHCID 5360545SodiumHCID 985544514502-66-0HCID 10942334Sodium Methoxide

Product 1

HCID 179326965-Formylaminomethyl-3-methylisoxazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
5 °C

Procedure

A stirred solution of nitroethane (17.9 ml, 0.25 mol) in N,N-dimethylacetamide (DMA) (250 ml) was added dropwise at 25°-30° C. to a solution of sodium methoxide, prepared by dissolving sodium (5.75 g) in dry methanol. The reaction mixture was cooled to 5° C. and acetyl chloride (18.5 ml, 0.26 mol) was added at 5°-10° C. Then was added a solution of 3-formylaminopropyn (17 g, 0.20 mol) in DMA (15 ml), and stirring was continued at room temperature overnight. The solvent was removed in vacuo and the residue was extracted with ether (300 ml). The ether was evaporated leaving an oily residue from which the title compound was isolated by distillation (120°-140° C./0.3 mmHg); 1H-NMR (CDCl3) 2.21 (s,3H), 4.35 (d,2H), 5.97 (s,1H), 7-8 (br, 1H), 8.13 (s,1H). (Compound 15).

Workup

  1. customprepared
  2. customThe solvent was removed in vacuo
  3. extractionthe residue was extracted with ether (300 ml)
  4. customThe ether was evaporated

Sources & evidence

ORD record
ord-696d3c6fac014446b44ee9b72b32d537
Source dataset
uspto-grants-1992_05
Patent number
US05116841

Reaction notes

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