3,4-Thiophenediacetonitrile, 2,5-dimethyl- → [2,5-Dimethyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetonitrile

HRID 900982

반응식

HRID 900982 반응식
[C:1]([CH2:3][C:4]1[C:5]([CH2:11][C:12]#[N:13])=[C:6]([CH3:10])[S:7][C:8]=1[CH3:9])#[N:2].Cl.N[C:16]1[C:21]([F:22])=[C:20]([F:23])[CH:19]=[C:18]([F:24])[C:17]=1[SH:25]>CCO>[CH3:9][C:8]1[S:7][C:6]([CH3:10])=[C:5]([CH2:11][C:12]2[S:25][C:17]3[C:18]([F:24])=[CH:19][C:20]([F:23])=[C:21]([F:22])[C:16]=3[N:13]=2)[C:4]=1[CH2:3][C:1]#[N:2]

참가 물질

4

반응물 2

HCID 8190183,4-Thiophenediacetonitrile, 2,5-dimethyl-HCID 11390282Benzenethiol, 2-amino-3,4,6-trifluoro-, hydrochloride

생성물 1

HCID 59698813[2,5-Dimethyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetonitrile수율 31.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of (4-cyanomethyl-2,5-dimethyl-thiophen-3-yl)-acetonitrile (1.90 g, 10.0 mmol) and 2-amino-3,4,6-trifluoro-benzenethiol hydrochloride (2.16 g, 10.0 mmol) in EtOH (22 mL) is heated to reflux for 44 h. After cooling to room temperature, the mixture is concentrated in vacuo and purified by flash chromatography (silica gel, 10-30% ethyl acetate in heptane). Further purification by recrystallization with ethyl acetate and heptane gave [2,5-dimethyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetonitrile (1.1 g, 31.2%) as a white powder: mp 145-146° C.; Rf 0.54 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ 6.95-7.08 (m, 1 H), 4.36 (s, 2 H), 3.59 (s, 2 H), 2.43 (s, 3 H), 2.41 (s, 3 H).

후처리

  1. temperatureto reflux for 44 h
  2. concentrationthe mixture is concentrated in vacuo
  3. custompurified by flash chromatography (silica gel, 10-30% ethyl acetate in heptane)
  4. customFurther purification
  5. customby recrystallization with ethyl acetate and heptane

출처 및 근거

ORD 기록
ord-c767adab3d1a47d98d79fc17ebadb3bd
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361671B2

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