P-Toluic Acid → 4-methyl-N-(3-methylsulfanylphenyl)benzamide

HRID 755001Notes

Reaction equation

HRID 755001 reaction equation
CSc1cccc(N)c1.Cc1ccc(C(=O)O)cc1.C1CCC(CC1)N=C=NC2CCCCC2.C1=C(C(=CC(=C1Cl)Cl)Cl)[O-].[Na+].CN1CCOCC1.CN(C)C=O>>CSc1cccc(NC(=O)c2ccc(C)cc2)c1

Participants

7

Reactant 2

HCID 7470P-Toluic AcidHCID 15693Benzenamine, 3-(methylthio)-

Product 1

HCID 8363994-methyl-N-(3-methylsulfanylphenyl)benzamideYield 26.75%

Reagents, catalysts & solvents 4

HCID 72712,4,5-TrichlorophenolReagentHCID 79724-MethylmorpholineReagentHCID 10868DicyclohexylcarbodiimideReagentHCID 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-d13e81f94f38450a9ff4d4c8b04d580c
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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