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Acetyl chloride → 5-Formylaminomethyl-3-methylisoxazole

HRID 1196858
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HRID 1196858 반응식
[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]
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참가 물질

8

반응물 5

HCID 6367Acetyl chlorideHCID 6587NitroethaneHCID 5360545SodiumHCID 9855445N-(prop-2-yn-1-yl)formamideHCID 10942334Sodium Methoxide

생성물 1

HCID 179326965-Formylaminomethyl-3-methylisoxazole

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 31374Dimethylacetamide용매2회

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온도
5 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-696d3c6fac014446b44ee9b72b32d537
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05116841

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