Pyridine → HCID 22592288, 화합물

HRID 22870

반응식

HRID 22870 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 22592288HCID 22592288, 화합물수율 51%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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])

출처 및 근거

ORD 기록
ord-65daf1c7ed2e423e80a6a7402d8e3650
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849648B2

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