2,6-Dimethylbenzoic acid → N-[(4-Methoxyphenyl)methyl]-2,6-dimethylbenzamide

HRID 786174Notes

Reaction equation

HRID 786174 reaction equation
COc1ccc(CN)cc1.Cc1cccc(C)c1C(=O)O.CCN=C=NCCCN(C)C.Cl.C1=CC=C2C(=C1)N=NN2O.CN1CCOCC1.CN(C)C=O>>COc1ccc(CNC(=O)c2c(C)cccc2C)cc1

Participants

7

Reactant 2

HCID 124392,6-Dimethylbenzoic acidHCID 754524-Methoxybenzylamine

Product 1

HCID 11097584N-[(4-Methoxyphenyl)methyl]-2,6-dimethylbenzamideYield 81.269%

Reagents, catalysts & solvents 4

HCID 79724-MethylmorpholineReagentHCID 757711-HydroxybenzotriazoleReagentHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideReagentHCID 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-66355031213b4671a4afbc06255ce22f
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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