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

HRID 1047139ノート

反応式

HRID 1047139 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 99.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5d2a52f3cd224c85931abee710a0e525
出典データセット
uspto-grants-2013_10
特許番号
US08569484B2

反応ノート

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