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

HRID 1047139노트

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HRID 1047139 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 99.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
40 °C

실험 절차

Methyl 2-amino-5-bromoisonicotinate (200 g, 865 mmol) was dissolved in chloroform (1.2 L) and placed into a 2 L Parr apparatus. Ethyl isocyanate (204 mL, 2.59 mol) was added, and the Parr apparatus was heated at 40° C. for 36 h at which time the reaction was determined to be complete. The mixture was then cooled to room temperature, concentrated, and the solid was dissolved in 2:1 ethyl acetate: tetrahydrofuran (3 L). This solution was extracted with water (1 L), and the water was back extracted with ethyl acetate (300 mL). The organic layers were combined then dried over sodium sulfate, filtered, and concentrated yielding 261 g (quant) of methyl 5-bromo-2-(3-ethylureido)isonicotinate as a dark yellow solid.

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionthe solid was dissolved in 2:1 ethyl acetate
  4. extractionThis solution was extracted with water (1 L)
  5. extractionthe water was back extracted with ethyl acetate (300 mL)
  6. dry with materialThe organic layers were combined then dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5d2a52f3cd224c85931abee710a0e525
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569484B2

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