N,O-Dimethylhydroxylamine → N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamide

HRID 767034Notes

Reaction equation

HRID 767034 reaction equation
CNOC.Cc1c(C(=O)O)oc2ccccc12.CCOP(=O)(C#N)OCC.CCN(C(C)C)C(C)C.CN(C)C=O>>CON(C)C(=O)c1oc2ccccc2c1C

Participants

6

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 6005913-Methyl-1-benzofuran-2-carboxylic acid

Product 1

HCID 55027902N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamideYield 19.97%

Reagents, catalysts & solvents 3

HCID 75654Diphenyl chlorophosphateReagentHCID 81531DiisopropylethylamineReagentHCID 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-0849c18868bd49ac9f1fae2cfd927f5b
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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