3-(Dimethylamino)propyl chloride hydrochloride → {5-[4-(3-Dimethylamino-propoxy)-phenyl]-thiazol-2-yl}phenyl-amine

HRID 1713647ノート

反応式

HRID 1713647 の反応式
[C:1]1([NH:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26].CC(C)([O-])C.[Na+]>C(O)CCC>[CH3:26][N:25]([CH3:27])[CH2:24][CH2:23][CH2:22][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[S:9][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:12][CH:11]=2)=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 23676156Sodium t-butoxideHCID 589235364-(2-Phenylamino-thiazol-5-yl)-phenol

生成物 1

HCID 11245147{5-[4-(3-Dimethylamino-propoxy)-phenyl]-thiazol-2-yl}phenyl-amine

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-(2-phenylamino-thiazol-5-yl)-phenol (35 mg, 0.130 mmol), 1-chloro-3-dimethylaminopropane hydrochloride (27 mg, 0.170 mmol, 1.3 equiv), and sodium tert-butoxide (29.6 mg, 0.299 mmol, 2.3 equiv) in 1-butanol (0.2 mL) is heated to 100° C. (using a preheated oil bath) for 3.5 h. The reaction mixture is allowed to cool to RT and concentrated in vacuo. Purification of the crude material by silica gel (10 g) column chromatography (CH2Cl2/MeOH, 90/10→80/20) affords the title compound as a reddish solid: ES-MS: 354.0 [M+H]+; single peak at tR=6.27 min (System 1); Rf=0.09 (CH2Cl2/MeOH, 90/10).

後処理

  1. temperatureto cool to RT
  2. concentrationconcentrated in vacuo
  3. customPurification of the crude material by silica gel (10 g) column chromatography (CH2Cl2/MeOH, 90/10→80/20)

出典と根拠

ORDレコード
ord-4f0ba443b1ea4751a27bc7830cb89a2e
出典データセット
uspto-grants-2010_09
特許番号
US07795288B2

反応ノート

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