1-Naphthaleneacetamide → 2-(naphthalen-1-yl)-N-(thiophen-3-yl)acetamide

HRID 2098185

반응식

HRID 2098185 반응식
[C:1]1([CH2:11][C:12]([NH2:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.I[C:16]1[CH:20]=[CH:19][S:18][CH:17]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C>[C:1]1([CH2:11][C:12]([NH:14][C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

8

반응물 4

HCID 68611-NaphthaleneacetamideHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 663323-Iodothiophene

생성물 1

HCID 687555152-(naphthalen-1-yl)-N-(thiophen-3-yl)acetamide수율 95%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

2-(naphthalen-1-yl)acetamide (14.00 g, 75.6 mmol), 3-iodothiophene (10.15 g, 48.3 mmol), trans-1,2diaminocyclohexane (3.0 ml, 25.0 mmol), cuprous iodide (1.97 g, 10.3 mmol), and potassium carbonate (13.66 g, 98.8 mmol) in dioxane (50 ml) was placed into a preheated oil bath at 95° C. After stirring for 18 h, the heterogenous mixture was diluted with water and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was flash chromatographed with 19:1, 9:1, 17:3, and 4:1 methylene chloride:ethyl acetate as the eluant to yield 12.26 g (95% yield) of 2-(naphthalen-1-yl)-N-(thiophen-3-yl)acetamide as a brown solid. Method [7] Retention time 2.07 min by HPLC (MH+ 268).

후처리

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 19:1, 9:1, 17:3, and 4:1 methylene chloride

출처 및 근거

ORD 기록
ord-dcf2d6c5651f4a6ba49b55b23785ae7d
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450363B2

연결된 노트

불러오는 중…