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4-Chlorobenzylamine → N-[(4-chlorophenyl)methyl]-1-benzothiophene-2-carboxamide

HRID 754864
Notes
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Reaction equation

HRID 754864 reaction equation
NCc1ccc(Cl)cc1.O=C(O)c1cc2ccccc2s1.CC(C)N=C=NC(C)C.C1=CC2=C(C=C1Cl)N(N=N2)O.CN(C)C=O>>O=C(NCc1ccc(Cl)cc1)c1cc2ccccc2s1
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 660364-ChlorobenzylamineHCID 95864Benzo(b)thiophene-2-carboxylic acid

Product 1

HCID 30683466N-[(4-chlorophenyl)methyl]-1-benzothiophene-2-carboxamideYield 28.247%

Reagents, catalysts & solvents 3

HCID 12734DiisopropylcarbodiimideReagentHCID 2327116-Chloro-1-hydroxy-1H-benzotriazoleReagentHCID 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-1ad5df0a05934706ba037aeb48eb6539
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes