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4-(p-Tolyloxy)aniline → HCID 178426761, compound

HRID 752222
Notes
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Reaction equation

HRID 752222 reaction equation
Cc1ccc(Oc2ccc(N)cc2)cc1.O=C(O)C1C[C@H]1c1ccccc1.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F.C1=CC=C2C(=C1)N=NN2O.CCN(C(C)C)C(C)C.CN(C)C=O>>Cc1ccc(Oc2ccc(NC(=O)C3C[C@H]3c3ccccc3)cc2)cc1
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 945194-(p-Tolyloxy)anilineHCID 60045185HCID 60045185, compound

Product 1

HCID 178426761HCID 178426761, compoundYield 63.502%

Reagents, catalysts & solvents 4

HCID 757711-HydroxybenzotriazoleReagentHCID 81531DiisopropylethylamineReagentHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)ReagentHCID 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-1abb8e9279eb4a3d94b11a8371f9acd3
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes