Tetrahydrofuran → HCID 86632878, compound

HRID 1398834Notes

Reaction equation

HRID 1398834 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C>[N+:13]([C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:16]([O-:18])=[O:17])[C:7]=1[NH:1][CH2:2][CH2:3][CH2:4][OH:5])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 118141-Chloro-2,6-dinitrobenzene

Product 1

HCID 86632878HCID 86632878, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-amino-1-propanol (6.77 mL, 89.0 mmol), 2-chloro-1,3-dinitrobenzene (15.0 g, 74.1 mmol), triethylamine (12.4 mL, 89.0 mmol) and tetrahydrofuran (370 mL) was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound as a solid (17.7 g, 73.3 mmol, 99%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4d848008e5b455cbb801170dab929bc
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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