Sodium Hydroxide → HCID 57525626、化合物

HRID 1594398ノート

反応式

HRID 1594398 の反応式
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[CH3:10][O:11][C:12]1([O:21][CH3:22])[CH2:15][CH:14]([C:16](=O)[CH2:17][C:18]#[N:19])[CH2:13]1>CCO>[C:2]([N:6]1[C:18]([NH2:19])=[CH:17][C:16]([CH:14]2[CH2:15][C:12]([O:11][CH3:10])([O:21][CH3:22])[CH2:13]2)=[N:7]1)([CH3:5])([CH3:4])[CH3:3]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 81889tert-Butylhydrazine monohydrochlorideHCID 575256253-(3,3-Dimethoxy-cyclobutyl)-3-oxo-propionitrile

生成物 1

HCID 57525626HCID 57525626、化合物収率 86%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
75 °C

実験手順

To a slurry of tert-butylhydrazine hydrochloride (45.1 g, 362.0 mmol) in EtOH (1 L) was added NaOH pellets (12.4 g, 310.3 mmol). After 30 min, crude 3-(3,3-dimethoxy-cyclobutyl)-3-oxo-propionitrile in EtOH (300 mL) was added. The resulting slurry was heated to 75° C. (oil bath). After 14 hr, the reaction was cooled to room temperature, filtered, and concentrated under reduced pressure. Isopropyl ether was added to the resulting slurry. The slurry was stirred for 15 min, filtered, and concentrated to yield a viscous oil. Trituration with ether/hexanes (several crops) gave the title compound (56.2 g, 86% yield over two steps) as a colorless solid: mp 80.9° C. 500 MHz 1H NMR (CDCl3) d 5.50 (s, 1H), 3.51 (bs, 2H), 3.18 (s, 3H), 3.16 (s, 3H), 3.19-3.14 (m, 1H), 2.60-2.54 (m, 2H), 2.20-2.14 (m, 2H), 1.59 (s, 9H). LRMS m/z (APCI+) 254 (M+1).

後処理

  1. waitAfter 14 hr
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionIsopropyl ether was added to the resulting slurry
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a viscous oil

出典と根拠

ORDレコード
ord-8fe61927dc7642568b2a8ae8f5eba017
出典データセット
uspto-grants-2007_11
特許番号
US07300944B2

反応ノート

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