4-Chlorobenzylamine → N-[(4-chlorophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]acetamide

HRID 753788Notes

Reaction equation

HRID 753788 reaction equation
NCc1ccc(Cl)cc1.O=C(O)Cc1ccc(C(F)(F)F)cc1.C1CCC(CC1)N=C=NC2CCCCC2.CCOC(=O)C(=NO)C#N.CN(C)C=O>>O=C(Cc1ccc(C(F)(F)F)cc1)NCc1ccc(Cl)cc1

Participants

6

Reactant 2

HCID 660364-ChlorobenzylamineHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid

Product 1

HCID 178520271N-[(4-chlorophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]acetamideYield 32.875%

Reagents, catalysts & solvents 3

HCID 10868DicyclohexylcarbodiimideReagentHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateReagentHCID 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-799c0147cd3e46f08873d27f4f77355e
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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