Triethylamine → N-[2-(2-cyanophenylthio)phenyl]-4-hexyloxybenzamide

HRID 1609279Notes

Reaction equation

HRID 1609279 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12].C(N(CC)CC)C.[CH2:24]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])O.[Na+]>CCOCC.O>[C:11]([C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:35](=[O:36])[C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:39][CH:38]=1)#[N:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 170235Benzoyl chloride, 4-(hexyloxy)-HCID 3662332-(2-Aminophenyl)sulfanylbenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 20084446N-[2-(2-cyanophenylthio)phenyl]-4-hexyloxybenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

In 2 ml of thionyl chloride was dissolved 1.03 g of 4-hexyloxybenzoic acid and the solution was refluxed for 1 hour. The excess thionyl chloride was distilled off and the residue was dried in vacuo to give 4-hexyloxybenzoyl chloride. Separately, 1.00 g of 2-(2-aminophenylthio)benzonitrile and 0.89 g of triethylamine were dissolved in 10 ml of ether and while the solution was stirred with ice-cooling, a solution of the above 4-hexyloxybenzoyl chloride in 5 ml of ether was added. The mixture was stirred overnight. Next morning, water and an aqueous solution of sodium hydrogen carbonate were added in the order mentioned and the resulting precipitate was extracted with ethyl acetate. The extract was dried over magnesium sulfate, the solvent was distilled off, and the residue was recrystallized from ethyl acetate-n-hexane to give 1.27 g of the title compound as white prisms.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred overnight
  3. extractionthe resulting precipitate was extracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customthe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-184eca3d198a440d8313b9ed88843970
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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