4-(Bromoacetyl)benzonitrile → 4-[2-(1-Phenylcyclopropyl)-1,3-thiazol-5-yl]benzonitrile

HRID 1592961노트

반응식

HRID 1592961 반응식
[C:1]1([C:7]2([C:10](=[S:12])[NH2:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][C:15]([C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)=O>CCO>[C:1]1([C:7]2([C:10]3[S:12][C:15]([C:17]4[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=4)=[CH:14][N:11]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 160935311-Phenylcyclopropane-1-carbothioamide

생성물 1

HCID 113471904-[2-(1-Phenylcyclopropyl)-1,3-thiazol-5-yl]benzonitrile

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

1-Phenylcyclopropanecarbothioamide (1-2, 0.050 g, 0.282 mmol) and 4-(bromoacetyl)benzonitrile (1-3, 0.063 g, 0.282 mmol) were combined in a dry flask, and dissolved in EtOH (10.0 mL). The resulting solution was refluxed for 2 h, and the product precipitated from the reaction upon cooling. The solid was filtered, washed with EtOH (3×5 mL) and dried under vacuum to provide 4-[2-(1-phenylcyclopropyl)-1,3-thiazol-5-yl]benzonitrile (1-4) as a tan solid: 1H NMR (300 MHz, CDCl3) δ 7.98 (d, J=8.2 Hz, 2H), 7.68 (d, J=8.2 Hz, 2H), 7.51 (d, J=7.6 Hz, 2H), 7.39 (m, 4H), 1.86 (dd, J=6.8, 3.9 Hz, 2H), 1.48 (dd, J=6.8, 3.9 Hz, 2H); MS 303.0 found 305.2 (M+H+) required.

후처리

  1. temperatureThe resulting solution was refluxed for 2 h
  2. customthe product precipitated from the reaction
  3. temperatureupon cooling
  4. filtrationThe solid was filtered
  5. washwashed with EtOH (3×5 mL)
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-4dc2bd20cfce49588b5efab35100872b
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294640B2

반응 노트

불러오는 중…