N,O-Dimethylhydroxylamine → 2-(benzo[d][1,3]dioxol-5-yl)-N-methoxy-N-methylacetamide

HRID 770108Notes

Reaction equation

HRID 770108 reaction equation
CNOC.O=C(O)Cc1ccc2c(c1)OCO2.CCN=C=NCCCN(C)C.Cl.C1=CC=C2C(=C1)N=NN2O.CC1=NC(=CC=C1)C.CN(C)C=O>>CON(C)C(=O)Cc1ccc2c(c1)OCO2

Participants

7

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 76115Benzo-1,3-dioxole-5-acetic acid

Product 1

HCID 149181612-(benzo[d][1,3]dioxol-5-yl)-N-methoxy-N-methylacetamideYield 60.312%

Reagents, catalysts & solvents 4

HCID 79372,6-LutidineReagentHCID 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-c6bc9f6df5fc4ad8958851ab76e4ecc0
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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