Triethylamine → HCID 67494921, compound

HRID 241416Notes

Reaction equation

HRID 241416 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.C(N(CC)CC)C.[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[F:31])[C:25](Cl)=[O:26].C(OCC)(=O)C>O1CCOCC1>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:30]([F:31])=[C:22]([F:21])[CH:23]=2)=[CH:5][C:6]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27245193,4-Difluorobenzoyl chlorideHCID 10442314HCID 10442314, compound

Product 1

HCID 67494921HCID 67494921, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

480 mg (2.649 mmol) of 4-(2-aminoethyl)-2-nitrophenylamine are dissolved in 30 ml of dioxane, and 1.102 ml (7.950 mmol) of triethylamine are added. 0.334 ml (2.650 mmol) of 3,4-difluorobenzoyl chloride are then added dropwise, and the mixture is stirred at room temperature for 30 min. Ethyl acetate is added to the reaction mixture, which is then washed 3× with water, dried using sodium sulfate, filtered and distilled off to dryness, giving N-[2-(4-amino-3-nitrophenyl)ethyl]-3,4-difluorobenzamide; EI-MS [M]+ 321, which is hydrogenated further under standard conditions, giving N-[2-(3,4-diaminophenyl)ethyl]-3,4-difluorobenzamide; HPLC-MS [M+H]+ 292.2.

Workup

  1. washis then washed 3× with water
  2. customdried
  3. filtrationfiltered
  4. distillationdistilled off to dryness

Sources & evidence

ORD record
ord-9b9ca915667b4d1fb655e4bf0a0c228b
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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