Triethylamine → HCID 86632924, compound

HRID 1398942Notes

Reaction equation

HRID 1398942 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[N+:20]([C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:23]([O-:25])=[O:24])[C:14]=1[NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118141-Chloro-2,6-dinitrobenzeneHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 86632924HCID 86632924, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl (3-aminopropyl)carbamate (4.20 g, 24.1 mmol), 2-chloro-1,3-dinitrobenzene (4.07 g, 20.1 mmol) and triethylamine (5.60 mL, 40.2 mmol) in tetrahydrofuran (200 mL) was stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 30% ethyl acetate/n-hexane mixture to give a yellow solid (6.79 g, 20.0 mmol, 99.5%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with a 30% ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-5f7ae8c22c9f44219546ea1da2a0aaa7
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…