Triethylamine → 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline

HRID 1758258Notes

Reaction equation

HRID 1758258 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12])[C:2]#[CH:3].C(N(CC)CC)C.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](Cl)=[O:26]>ClCCl>[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]([N:4]([CH2:1][C:2]#[CH:3])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chloride2×HCID 2997052,6-dimethyl-N-prop-2-ynyl-aniline

Product 1

HCID 131504722,6-dimethyl-N-(2-furoyl)-N-propargyl-anilineYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 3.64 g (0.025 mole) of N-(2-propynyl)-2,6-dimethylbenzenamine and 2.52 g (0.025 mole) of triethylamine in 25 ml of dichloromethane is stirred rapidly under nitrogen at room temperature as 3.06 g (0.025 mole) of 2-furoyl chloride, dissolved in 5 ml of dichloromethane, is added at a moderate rate. Upon addition of the 2-furoyl chloride a vigorous exotherm is noted, causing the solvent to reflux for 2 min. The mixture is stirred for 30 min. and then poured into 200 ml of dichloromethane and washed with water (100 ml), 5% HCl (100 ml), water (100 ml) and brine (100 ml). The organic layer is dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to yield a solid. The solid is washed with n-hexane and vacuum dried to yield 3.65 g (0.0144 mole) of N-(2-furoyl)-N-(2-propynyl)-2,6-dimethylbenzenamine.

Workup

  1. additionis added at a moderate rate
  2. temperatureto reflux for 2 min
  3. washwashed with water (100 ml), 5% HCl (100 ml), water (100 ml) and brine (100 ml)
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customto yield a solid
  8. washThe solid is washed with n-hexane and vacuum
  9. customdried

Sources & evidence

ORD record
ord-7146dc95cb0446c7a24a9879634d4f28
Source dataset
uspto-grants-1983_02
Patent number
US04372972

Reaction notes

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