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

HRID 2061843ノート

反応式

HRID 2061843 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
40 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8500ddfcbfb94a56a01f6f71dbe6fa35
出典データセット
uspto-grants-2012_10
特許番号
US08283361B2

反応ノート

読み込み中…