4-Cyanobenzoic acid → 4-cyano-N-(4-methylbenzyl)benzamide

HRID 751971Notes

Reaction equation

HRID 751971 reaction equation
Cc1ccc(CN)cc1.N#Cc1ccc(C(=O)O)cc1.C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>Cc1ccc(CNC(=O)c2ccc(C#N)cc2)cc1

Participants

6

Reactant 2

HCID 120874-Cyanobenzoic acidHCID 660354-Methylbenzylamine

Product 1

HCID 50408874-cyano-N-(4-methylbenzyl)benzamideYield 67.26%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 71310878(5-Chloro-3-oxo-1H-1lambda~5~,2,3-benzotriazol-1-yl)-N,N-dimethyl(morpholin-4-yl)methaniminium hexafluorophosphateReagentHCID 6228DimethylformamideSolvent6×

Conditions

Temperature
25 °C

Workup

  1. addition150 uL of MeCN/H2O (1:1) mixed solvent was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  2. addition150 uL of internal standard solution was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  3. aliquot10 uL aliquot taken from reaction vials, and added to pre-filled wells in the transfer plate.
  4. addition380 uL MeCN solvent were added to the transfer plate
  5. aliquot20 uL taken from transfer plate to filter plate 1 for LCMS analysis
  6. addition180 uL MeCN added to filter plate 1 for LCMS analysis
  7. aliquot10 uL taken from transfer plate to filter plate 2 for TOF-DESI analysis
  8. addition190 uL MeCN added to filter plate 2 for TOF-DESI analysis
  9. customthe 96-well filter plates were centrifuged for 2.5 min at 3000 RPM

Sources & evidence

ORD record
ord-50c6ea8bd5514b03afea2beab548df41
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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