N-BOC-ethylenediamine → HCID 178453698, compound

HRID 1085842Notes

Reaction equation

HRID 1085842 reaction equation
[C:1]1([C:7]2[C:8]([C:12]([O:14]CC)=O)=[N:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>C(O)C>[C:1]1([C:7]2[C:8]([C:12]([NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:14])=[N:9][NH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 178470485HCID 178470485, compound

Product 1

HCID 178453698HCID 178453698, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 g (23.12 mmol) of ethyl 4-phenyl-3-pyrazolecarboxylate were heated to 120° under reduced pressure for hours with 7.4 g (46.19 mmol) of t-butyl (2-aminoethyl)carbamate, whereby the ethanol formed was distilled off continuously. The reaction mixture was then taken up in methylene chloride and chromatographed on 150 g of silica gel with a 9:1, 8:2 and 7:3 mixture of methylene chloride and ethyl acetate as the eluting agent. The fractions which were pure according to the thin-layer chromatogram were combined and evaporated, and the residue was crystallized from ethyl acetate/hexane, whereby there were obtained 5.1 g (66.8%) of t-butyl [2-(4-phenylpyrazole-3carboxamido)ethyl]carbamate as white crystals, melting point 71°/162°-163° (still containing 0.05 mol of hexane).

Workup

  1. customformed
  2. distillationwas distilled off continuously
  3. customchromatographed on 150 g of silica gel with a 9:1, 8:2 and 7:3 mixture of methylene chloride and ethyl acetate as the eluting agent
  4. customevaporated
  5. customthe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4b68ee6d927d48ef91db2e24e7655d9b
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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