Tetrahydrofuran → HCID 86632876, compound

HRID 1628476Notes

Reaction equation

HRID 1628476 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].Cl[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C>[N+:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:18]([O-:20])=[O:19])[C:9]=1[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 118141-Chloro-2,6-dinitrobenzeneHCID 756345-Aminopentan-1-ol2×

Product 1

HCID 86632876HCID 86632876, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-amino-1-pentanol (619 mg, 6.00 mmol), 2-chloro-1,3-dinitrobenzene (1.01 g, 4.99 mmol), triethylamine (0.837 mL, 6.01 mmol) and tetrahydrofuran (20 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added 5-amino-1-pentanol (520 mg, 5.04 mmol) at room temperature and the resultant mixture was stirred at room temperature for 0.5 hr. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture to give the title compound as a yellow oil (1.30 g, 4.82 mmol, 97%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-e6e58282161b42839296c04b9de321c3
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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