Acetyl chloride → N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]acetamide

HRID 1958025

反応式

HRID 1958025 の反応式
[NH2:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][C:6]=1[C:7]#[N:8].[C:15](Cl)(=[O:17])[CH3:16]>N1C=CC=CC=1>[C:7]([C:6]1[S:5][C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:3][C:2]=1[NH:1][C:15](=[O:17])[CH3:16])#[N:8]

参加物

4

反応物 2

HCID 6367Acetyl chlorideHCID 21319839HCID 21319839、化合物

生成物 1

HCID 66780286N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]acetamide収率 82%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

To a 5 L round bottom flask equipped with a mechanical stirrer was added 4-amino-2-(4-morpholinyl)-1,3-thiazole-5-carbonitrile (200 g, 951 mmol) and N,N-dimethylaminopyridine (23.24 g, 190 mmol). The solids were taken up in Pyridine (2000 mL) and to this reaction solution was added acetyl chloride (74.7 g, 951 mmol) via an addition funnel. The reaction was heated to 80° C. and monitored by LCMS for conversion to product. Upon complete conversion (˜2 hours), the reaction was cooled to room temperature and the reaction was concentrated to a slurry, then subsequently diluted with a mixture of 0.1N NaOH (2 L) solution and methanol (140 mL). The mixture was rapidly stirred using a mechanical stirrer for 15 min, then the resulting precipitate was collected by filtration to provide the desired N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]acetamide (218.2 g, 778 mmol, 82% yield) as a brown solid (1H NMR (400 MHz, DMSO-d6) δ ppm 2.04 (s, 3H) 3.40-3.53 (m, 4H) 3.62-3.77 (m, 4H) 10.88 (s, 1H)).

後処理

  1. customTo a 5 L round bottom flask equipped with a mechanical stirrer
  2. temperatureUpon complete conversion (˜2 hours), the reaction was cooled to room temperature
  3. concentrationthe reaction was concentrated to a slurry
  4. additionsubsequently diluted with a mixture of 0.1N NaOH (2 L) solution and methanol (140 mL)
  5. customfor 15 min
  6. filtrationthe resulting precipitate was collected by filtration

出典と根拠

ORDレコード
ord-4d9358094ee74517b1de48ad53984aa7
出典データセット
uspto-grants-2013_04
特許番号
US08410095B2

関連ノート

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