Triethylamine → HCID 86589871, compound

HRID 2417469Notes

Reaction equation

HRID 2417469 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([CH:15]=1)[CH2:7][NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(N(CC)CC)C.[H][H]>ClCCl.C(OCC)(=O)C.[Pd]>[NH2:16][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][C:6]=1[CH2:7][N:8]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([Cl:19])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 67363323Ethyl (5-chloro-2-nitrobenzyl)aminoacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 86589871HCID 86589871, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.15 g (4.2 mmol) of ethyl (5-chloro-2-nitrobenzyl)aminoacetate was dissolved in 20 ml of dichloromethane. 0.64 ml (5.1 mmol) of 4-chlorobenzoyl chloride and 0.88 ml (6.3 mmol) of triethylamine were added to the obtained solution, and they were stirred at room temperature for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 20 ml of ethyl acetate. 120 mg of 10% palladium/carbon was added to the obtained solution and they were stirred in the presence of hydrogen at room temperature for 4 hours. The reaction solution was filtered through Celite. The solvent was evaporated and the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. customThe solvent was evaporated
  3. customthe obtained crude product
  4. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-957bf3f5a58d44bab349f22331d8ae27
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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