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

HRID 1713647노트

반응식

HRID 1713647 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4f0ba443b1ea4751a27bc7830cb89a2e
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795288B2

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