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

HRID 1958025

반응식

HRID 1958025 반응식
[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]

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 21319839HCID 21319839, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

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)).

후처리

  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

출처 및 근거

ORD 기록
ord-4d9358094ee74517b1de48ad53984aa7
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410095B2

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