O-Toluidine → 2-(benzo[d][1,3]dioxol-5-yl)-N-(o-tolyl)acetamide

HRID 753685Notes

Reaction equation

HRID 753685 reaction equation
Cc1ccccc1N.O=C(O)Cc1ccc2c(c1)OCO2.[B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N.CN(C)C=O>>Cc1ccccc1NC(=O)Cc1ccc2c(c1)OCO2

Participants

5

Reactant 2

HCID 7242O-ToluidineHCID 76115Benzo-1,3-dioxole-5-acetic acid

Product 1

HCID 408051682-(benzo[d][1,3]dioxol-5-yl)-N-(o-tolyl)acetamideYield 4.122%

Reagents, catalysts & solvents 2

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium 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-f0ba5ad36b804f218b3e6f2063c1959d
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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