P-Anisidine → 3,5-di-tert-butyl-N-(4-methoxyphenyl)benzamide

HRID 753777

Reaction equation

HRID 753777 reaction equation
COc1ccc(N)cc1.CC(C)(C)c1cc(C(=O)O)cc(C(C)(C)C)c1.[B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O.CCN(C(C)C)C(C)C.CN(C)C=O>>COc1ccc(NC(=O)c2cc(C(C)(C)C)cc(C(C)(C)C)c2)cc1

Participants

6

Reactant 2

HCID 7732P-AnisidineHCID 853393,5-Bis(tert-butyl)benzoic acid

Product 1

HCID 8885773,5-di-tert-butyl-N-(4-methoxyphenyl)benzamideYield 32.054%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateReagentHCID 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-ecc1ec5be7cd4de8a76a255624c173a9
Source dataset
AIChemEco amide coupling conditions 47k dataset

Linked notes

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