Hydrochloric Acid → 3-Pyridin-2-yl-isoxazole-4-carboxylic acid ethyl ester

HRID 332054

반응식

HRID 332054 반응식
Cl[N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=O.C[N:10]([CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])C.[CH2:19](N(CC)CC)C.Cl.CN([CH:30]=[O:31])C>C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([C:13]1[C:12]([C:6]2[CH:5]=[CH:4][CH:3]=[CH:19][N:2]=2)=[N:10][O:31][CH:30]=1)=[O:15])[CH3:18]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 121015Ethyl 3-(N,N-dimethylamino)acrylate

생성물 1

HCID 666437583-Pyridin-2-yl-isoxazole-4-carboxylic acid ethyl ester수율 66%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of N-chlorosuccinimide (54.7 g, 409 mmol) in DMF (1 L) was added pyridine-2-carbaldoxime (50 g, 409 mmol) portionwise and the resulting mixture was then stirred for 64 h at room temperature. To this solution was then added ethyl 3-(N,N-dimethylamino)acrylate (58.6 g, 409 mmol) and triethylamine (82.9 mL, 819 mmol) in chloroform (10 mL) and the resulting mixture was then stirred for 14 h at room temperature and poured onto a mixture of ice water and HCl (4 N, 100 mL) and extracted with ethylacetate. The organic extract was then washed with water, saturated aqueous sodium hydrogen carbonate solution, brine, dried with sodium sulfate, filtered and evaporated. Purification by distillation afforded the title product (58.9 g, 66%) which was obtained as a light brown liquid. Bp 125-127° C. at 0.4 mbar. MS: m/e=219.2 [M+H]+.

후처리

  1. extractionextracted with ethylacetate
  2. extractionThe organic extract
  3. washwas then washed with water, saturated aqueous sodium hydrogen carbonate solution, brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification
  8. distillationby distillation

출처 및 근거

ORD 기록
ord-23e3329218974e34b51ec3481441648b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877782B2

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