4-Aminobenzoic Acid → HCID 20027317, compound

HRID 1722711Notes

Reaction equation

HRID 1722711 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(N([CH2:16][CH3:17])CC)C.S(Cl)(Cl)=O.[CH2:22]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26][NH2:27])[CH3:23].[CH2:30](OCC)C>>[CH2:22]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26][NH:27][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:30][C:16]#[CH:17])=[CH:10][CH:9]=1)[CH3:23]

Participants

6

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 60993N,N-Diethylethylenediamine

Product 1

HCID 20027317HCID 20027317, compound

Procedure

To a refluxing solution of 4-aminobenzoic acid, 5 g (0.036 mol), and triethylamine, 11.1 g (0.11 mol), in diethyl ether is added dropwise thionyl chloride, 5.14 g (0.043 mol). After one hour, N,N-diethylethylenediamine, 6.28 g (0.054 mol), is added and the reaction is refluxed for another eight hours or until thin layer chromatography (TLC) indicates amide formation is complete. The solution is cooled to room temperature and filtered. The filtrate is washed with water and the organic layer is separated, dried (sodium sulfate), and filtered. The filtrate is concentrated in vacuo and the residue is dissolved in toluene. To this solution is added an 80% by weight solution of propargyl bromide in toluene, 10.7 g (0.072 mol), and triethylamine, 7.27 g (0.072 mol). The reaction is refluxed for twenty-four hours. Aqueous workup gives a crude mixture of mono and dialkylated benzamides which are separated by chromatography over silica gel to give the desired product.

Workup

  1. temperaturethe reaction is refluxed for another eight hours or until thin layer chromatography (TLC)
  2. filtrationfiltered
  3. washThe filtrate is washed with water
  4. customthe organic layer is separated
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo
  8. dissolutionthe residue is dissolved in toluene
  9. additionTo this solution is added an 80% by weight solution of propargyl bromide in toluene, 10.7 g (0.072 mol), and triethylamine, 7.27 g (0.072 mol)
  10. temperatureThe reaction is refluxed for twenty-four hours
  11. customAqueous workup gives a crude
  12. customare separated by chromatography over silica gel

Sources & evidence

ORD record
ord-4b3b21b0dae54820b162cb0e6e450156
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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