1-Fluoro-3-nitrobenzene → N-[6-(3-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

HRID 2190362ノート

反応式

HRID 2190362 の反応式
[OH:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([CH:12]3[CH2:14][CH2:13]3)=[O:11])[S:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=1.C1OCCOCCOCCOCCOCCOC1>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[N+:30]([C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[O:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([CH:12]3[CH2:13][CH2:14]3)=[O:11])[S:8][C:4]=2[CH:3]=1)([O-:32])=[O:31]

参加物

8

反応物 4

HCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 57980821HCID 57980821、化合物

生成物 1

HCID 57749256N-[6-(3-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide収率 36.2%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

To a suspension of N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamide (1.53 g, 6.53 mmol) and potassium carbonate (3.72 g, 26.9 mmol) in N,N-dimethylformamide (50 mL) were added 1-fluoro-3-nitrobenzene (1.08 g, 7.65 mmol) and 18-crown-6 (1.07 g, 4.05 mmol), and the mixture was stirred at 150° C. for 14 hr. The reaction mixture was cooled to room temperature, and added to a mixed solvent (1:1, 300 mL) of ethyl acetate and hexane. The mixture was washed with water (200 mL) and saturated brine (200 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was collected by filtration, and the residue was subjected to silica gel column chromatography using ethyl acetate and hexane (1:1) as an eluent to give the title compound (840 mg, 36%) as a pale-yellow solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe mixture was washed with water (200 mL) and saturated brine (200 mL)
  3. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was collected by filtration

出典と根拠

ORDレコード
ord-4623aad3604e4a868fe547e92e5bc920
出典データセット
uspto-grants-2012_12
特許番号
US08324395B2

反応ノート

読み込み中…