Triethylamine → HCID 178514512、化合物

HRID 626699ノート

反応式

HRID 626699 の反応式
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[CH:10]=O)=[N+:2]=[N-:3].[Cl:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([Cl:20])[C:14]=1[NH2:21].C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1/[CH:10]=[N:21]/[C:14]1[C:13]([Cl:12])=[CH:18][C:17]([F:19])=[CH:16][C:15]=1[Cl:20])=[N+:2]=[N-:3]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 27740082,6-Dichloro-4-fluoroanilineHCID 866970374-Azidopyridine-3-carbaldehyde

生成物 1

HCID 178514512HCID 178514512、化合物収率 99.8%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Titanium tetrachloride (1M, 4.0 mL, 4.15 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (1.0 g, 6.75 mmol), 2,6-dichloro-4-fluorophenylamine (1.22 g, 6.75 mmol) and triethylamine (2.8 mL, 20.3 mmol) in DCM (24 mL), under nitrogen. The reaction was stirred for 30 minutes at 0° C., warmed to room temperature, stirred for an additional 2 h, and concentrated under reduced pressure. The residue was dissolved in toluene and filtered though a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid (2.09 g, quant.). This crude material was employed in the next step without further purification or analysis.

後処理

  1. temperaturea cooled
  2. temperaturewarmed to room temperature
  3. stirringstirred for an additional 2 h
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in toluene
  6. filtrationfiltered though a pad of Celite®
  7. concentrationThe filtrate was concentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-95e5fc1900274ec280eaa8e0f08f5c1a
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

読み込み中…