Triethylamine → HCID 19702684, compound

HRID 1451667Notes

Reaction equation

HRID 1451667 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CC=CCN.C(N(CC)CC)C.[CH3:23][N:24]1C[CH2:27][CH2:26][C:25]1=O>O>[CH2:25]([N:24]([CH3:23])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 13387N-methyl-2-pyrrolidoneHCID 304472-Buten-1-amine

Product 1

HCID 19702684HCID 19702684, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of p-fluoronitrobenzene (2.8 g, 20 mmol), N-methylallylamine (2.10 g, 30 mmol), triethylamine (2.0 g, 20 mmol), and N-methyl-2-pyrrolidinone (NMP) (20 ml) was heated to 60°-70° C. for 5 hours in an oil bath. The mixture was diluted with distilled water (100 ml) and extracted twice with ether. The extracts were washed with distilled water and brine solution, dried over potassium carbonate and concentrated to an oil. The oil was distilled via Kugelrohr apparatus (forecut taken up to 90° C. discarded, 110°-125° C., 0.1 mm Hg) to give 3.70 g (96%) N-allyl-N-methyl-4-nitroaniline. As is, this material failed to undergo clean hydrosilation, possibly due to residual N-methyl-2-pyrrolidinone present. The remaining material was chromatographed on silica with hexane-ethyl acetate (10:1) and distilled again via Kugelrohr apparatus to give a yellow oil that underwent clean hydrosilation.

Workup

  1. temperaturewas heated to 60°-70° C. for 5 hours in an oil bath
  2. extractionextracted twice with ether
  3. washThe extracts were washed with distilled water and brine solution
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated to an oil
  6. distillationThe oil was distilled via Kugelrohr apparatus (forecut
  7. customtaken up to 90° C.
  8. customdiscarded, 110°-125° C.

Sources & evidence

ORD record
ord-b55d49a5a03d402ca83df3c4654a5b6f
Source dataset
uspto-grants-1997_02
Patent number
US05605726

Reaction notes

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