Triethylamine → HCID 20341217, compound

HRID 1395016Notes

Reaction equation

HRID 1395016 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].C(N(CC)CC)C.[CH:26]1([CH2:29][NH:30][CH2:31][CH3:32])[CH2:28][CH2:27]1>C(COC)OC>[CH:26]1([CH2:29][N:30]([CH2:31][CH3:32])[C:6]2[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]([C:15]([F:18])([F:17])[F:16])=[C:2]([Cl:1])[C:7]=2[N+:8]([O-:10])=[O:9])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzeneHCID 20341223N-(Cyclopropylmethyl)ethanamine

Product 1

HCID 20341217HCID 20341217, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 15.0 grams (0.05 mole) of 2,4-dichloro-3,5-dinitrobenzotrifluoride and 4.97 grams (0.05 mole) of triethylamine in 200 ml. of dimethoxyethane was added, dropwise, 4.28 grams (0.05 mole) of N-cyclopropylmethyl-N-ethylamine at room temperature over a period of 2.5 hours. The resultant mixture was then heated under reflux for 16 hours. The solvent was removed by evaporation under reduced pressure and the residue then dissolved in a mixture of chloroform and water. The organic layer was separated and was washed with water, dilute hydrochloric acid, dilute sodium bicarbonate, and then water. After drying over anhydrous sodium sulfate, the organic solution was evaporated to dryness. The residue was dissolved in hexane and filtered and then evaporated to dryness to give 12.85 grams of the product as as dark, viscous amber liquid.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe solvent was removed by evaporation under reduced pressure
  3. dissolutionthe residue then dissolved in a mixture of chloroform and water
  4. customThe organic layer was separated
  5. washwas washed with water, dilute hydrochloric acid, dilute sodium bicarbonate
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe organic solution was evaporated to dryness
  8. dissolutionThe residue was dissolved in hexane
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-137683e693ba4d71a69ab84c20f3be5f
Source dataset
uspto-grants-1980_05
Patent number
US04201724

Reaction notes

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