Ammonium sulfamate → Ethyl 2-chloromethyl-5-ethylnicotinate

HRID 1032818

반응식

HRID 1032818 반응식
[CH2:1]([O:3][C:4](=[O:11])[CH:5](Cl)[C:6]([CH2:8][Cl:9])=O)[CH3:2].[CH2:12]([C:14](=[CH2:17])[CH:15]=O)[CH3:13].S(=O)(=O)([O-])[NH2:19].[NH4+]>C(O)C>[Cl:9][CH2:8][C:6]1[N:19]=[CH:15][C:14]([CH2:12][CH3:13])=[CH:17][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:11]

참가 물질

5

반응물 3

HCID 24482Ammonium sulfamateHCID 70203EthylacroleinHCID 101546Ethyl 2,4-dichloro-3-oxobutanoate

생성물 1

HCID 14600680Ethyl 2-chloromethyl-5-ethylnicotinate수율 43.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 61 g of ethyl-2,4-dichloroacetoacetate (0.306 mol) and 30 g of 2-ethylacrolein (0.357 mol) in 500 mL of absolute ethanol is mixed with 85.5 g of ammonium sulfamate (0.75 mol), and the stirred mixture is heated at reflux for 90 minutes. The reaction is concentrated in vacuo and the residue is partitioned between ethyl acetate and water. The organic phase is concentrated in vacuo, and the residue is chromatographed on silica gel using hexane-ethyl acetate mixtures to give 50 g of crude product. This material is purified by extraction into aqueous hydrochloric acid, washing with hexanes, making the aqueous phase basic with cold ammonium hydroxide, and extracting with hexanes to afford 30 g of the title product as an oil (43%), having elemental analysis calculated for C11H14ClNO2 % C 58.03, H 6.20, N 6.15, Cl 15.57 found % C 58.29, H 6.30, N 6.02, Cl 15.49.

후처리

  1. temperaturethe stirred mixture is heated
  2. temperatureat reflux for 90 minutes
  3. concentrationThe reaction is concentrated in vacuo
  4. customthe residue is partitioned between ethyl acetate and water
  5. concentrationThe organic phase is concentrated in vacuo
  6. customthe residue is chromatographed on silica gel
  7. customto give 50 g of crude product
  8. customThis material is purified by extraction into aqueous hydrochloric acid
  9. washwashing with hexanes
  10. extractionextracting with hexanes

출처 및 근거

ORD 기록
ord-d17ece7ac57c423dbc0adc55fcf61259
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04959476

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