Ethyl isocyanate → Methyl 5-bromo-2-(3-ethylureido)isonicotinate

HRID 2061843노트

반응식

HRID 2061843 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([Br:12])=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>C(Cl)(Cl)Cl>[Br:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]([NH:1][C:16]([NH:15][CH2:13][CH3:14])=[O:17])=[N:11][CH:10]=1

참가 물질

4

반응물 2

HCID 8022Ethyl isocyanateHCID 25307230Methyl 2-amino-5-bromoisonicotinate

생성물 1

HCID 59416007Methyl 5-bromo-2-(3-ethylureido)isonicotinate수율 104.6%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
40 °C

실험 절차

A solution of methyl 2-amino-5-bromoisonicotinate (50 g, 216.5 mmol) in chloroform (500 mL) was placed into a sealed tube. Ethyl isocyanate (51 mL, 649.4 mmol) was then added in two parts over the course of 6 hours. The sealed tube was insulated and heated at 40° C. for 3 d. The reaction mixture was then cooled to room temperature, concentrated under reduced pressure, and extracted with ethyl acetate (3 L) and water (1 L). The ethyl acetate layer was then dried with sodium sulfate, filtered, and concentrated under reduced pressure to yield 68.4 g of a pale yellow solid (96%).

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate (3 L) and water (1 L)
  4. dry with materialThe ethyl acetate layer was then dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8500ddfcbfb94a56a01f6f71dbe6fa35
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283361B2

반응 노트

불러오는 중…