Cyanuric chloride → 4-Chlorothieno[2,3-b]pyridine-5-carbonitrile

HRID 1178613

반응식

HRID 1178613 반응식
[Cl:1][C:2]1[C:7]([C:8]([NH2:10])=O)=[CH:6][N:5]=[C:4]2[S:11][CH:12]=[CH:13][C:3]=12.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C)C=O>[Cl:1][C:2]1[C:7]([C:8]#[N:10])=[CH:6][N:5]=[C:4]2[S:11][CH:12]=[CH:13][C:3]=12

참가 물질

4

반응물 2

HCID 7954Cyanuric chlorideHCID 111485614-Chlorothieno[2,3-B]pyridine-5-carboxamide

생성물 1

HCID 114129074-Chlorothieno[2,3-b]pyridine-5-carbonitrile수율 63.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-chlorothieno[2,3-b]pyridine-5-carboxamide (145 mg, 0.68 mmol) and cyanuric chloride (200 mg, 1.08 mmol) in 5 mL of N,N-dimethylformamide is stirred at room temperature for 30 minutes. Ice is added to the reaction mixture and the resultant solids are collected by filtration washing with water to provide 84 mg of 4-chlorothieno[2,3-b]pyridine-5-carbonitrile as a white solid, mp 100–103° C.; 1H NMR (DMSO-d6) δ 7.66 (d, J=6 Hz, 1H), 8.26 (d, J=6 Hz, 1H), 9.03 (s, 1H); MS 195.0 (M+H)+.

후처리

  1. additionIce is added to the reaction mixture
  2. filtrationthe resultant solids are collected by filtration
  3. washwashing with water

출처 및 근거

ORD 기록
ord-68cbe3a5969d4df98e87fabf9a0fb916
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276519B2

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