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

HRID 900982

反応式

HRID 900982 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c767adab3d1a47d98d79fc17ebadb3bd
出典データセット
uspto-grants-2008_04
特許番号
US07361671B2

関連ノート

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