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

HRID 2098185

Reaction equation

HRID 2098185 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dcf2d6c5651f4a6ba49b55b23785ae7d
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Linked notes

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