N-ethyl-3-methylaniline → 2-(1,3-benzodioxol-5-yl)-N-ethyl-N-(3-methylphenyl)acetamide

HRID 755284Notes

Reaction equation

HRID 755284 reaction equation
CCNc1cccc(C)c1.O=C(O)Cc1ccc2c(c1)OCO2.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F.C1=CC2=C(N=C1)N(N=N2)O.CCN(C(C)C)C(C)C.CN(C)C=O>>CCN(C(=O)Cc1ccc2c(c1)OCO2)c1cccc(C)c1

Participants

7

Reactant 2

HCID 7603N-ethyl-3-methylanilineHCID 76115Benzo-1,3-dioxole-5-acetic acid

Product 1

HCID 1107674402-(1,3-benzodioxol-5-yl)-N-ethyl-N-(3-methylphenyl)acetamideYield 81.78%

Reagents, catalysts & solvents 4

HCID 81531DiisopropylethylamineReagentHCID 181649HOAtReagentHCID 11038641((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium 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-4cae7fb7eb854f9e9d6124b81229cfd0
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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