Pyridine → HCID 22592288、化合物

HRID 22870

反応式

HRID 22870 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].Cl.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1)#[N:13].N1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C.Cl>[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)=[CH:16][CH:15]=1)#[N:13]

参加物

7

反応物 3

HCID 1049PyridineHCID 743783-Iodobenzoyl chlorideHCID 99422504-(Aminomethyl)benzonitrile hydrochloride

生成物 1

HCID 22592288HCID 22592288、化合物収率 51%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

An aliquot of 3-iodobenzoyl chloride (1.1 g, 4.2 mmol) was taken up in tetrahydrofuran (“THF”, 25 mL), and cooled to approximately 0° C. in an ice-water bath. To the cold solution were added 4-cyanobenzylamine hydrochloride (0.71 g, 4.2 mmol) and pyridine (0.66 g, 8.3 mmol). The solution gradually warmed to room temperature, and was stirred for 72 hours. The reaction mixture was diluted with ethyl acetate (25 mL) and aqueous HCl (25 mL). The organic phase was separated, dried (MgSO4), filtered, and rotary evaporated. The resulting crude product was purified using silica gel chromatography (elution with dichloromethane/THF [9:1]) to give N-(4-cyano-benzyl)-3-iodo-benzamide (0.76 g, 51%) as a white solid. 1H-NMR (DMSO-d6) δ 9.2 (t, 1H), 8.2 (s, 1H), 7.9 (m, 2H), 7.8 (d, 2H), 7.5 (d, 2H), 7.3 (m, 1H), 4.5 (d, 2H) ppm.

後処理

  1. temperatureThe solution gradually warmed to room temperature
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe resulting crude product was purified
  6. washsilica gel chromatography (elution with dichloromethane/THF [9:1])

出典と根拠

ORDレコード
ord-65daf1c7ed2e423e80a6a7402d8e3650
出典データセット
uspto-grants-2005_02
特許番号
US06849648B2

関連ノート

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