Acetic Anhydride → 3-(2-Nitro-5-(thiophen-2-yl)phenyl)urea

HRID 62693Notes

Reaction equation

HRID 62693 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][C:12]=1[NH:22][C:23]([NH:25]CC1CCNCC1)=[O:24])([O-:10])=[O:9].C(N(CC)CC)C>ClCCl.O>[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][C:12]=1[NH:22][C:23](=[O:24])[NH2:25])([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 709815901-(2-Nitro-5-(thiophen-2-yl)phenyl)-3-(piperidin-4-ylmethyl)urea

Product 1

HCID 867125323-(2-Nitro-5-(thiophen-2-yl)phenyl)ureaYield 122.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.03 g, 0.31 mmol, 1.1 equiv.) was added to a solution of 1-(2-nitro-5-(thiophen-2-yl)phenyl)-3-(piperidin-4-ylmethyl)urea (0.10 g, 0.28 mmol, 1.0 equiv.) and triethylamine (60 μL, 0.42 mmol, 1.5 equiv.) in dichloromethane (5 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 h. The reaction was then diluted with water. The product was extracted with dichloromethane, washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude solid was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2) to afford 14(1-acetylpiperidin-4-yl)methyl)-3-(2-nitro-5-(thiophen-2-yl)phenyl)urea (0.09 g, 81% yield).

Workup

  1. extractionThe product was extracted with dichloromethane
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude solid was purified by column chromatography (silica gel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-eaa035cccda5468a910111ce69c9fa36
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Reaction notes

Loading…