Hydrochloric Acid → 4-[2-(4-Nitrobenzoylamino)benzoylamino]butanoic acid

HRID 2374715Notes

Reaction equation

HRID 2374715 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5].C[Si](Cl)(C)C.C(N(CC)CC)C.[N+:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)([O-:31])=[O:30].[OH-].[Na+].Cl>C(Cl)Cl.C(OCC)(=O)C>[N+:29]([C:32]1[CH:33]=[CH:34][C:35]([C:36]([NH:1][C:2]2[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=2[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5])=[O:37])=[CH:39][CH:40]=1)([O-:31])=[O:30]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 14798Sodium HydroxideHCID 134423754-(2-Aminobenzamido)butanoic acid

Product 1

HCID 231185624-[2-(4-Nitrobenzoylamino)benzoylamino]butanoic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2.14 g (9.63 mmol) of 4-(2-aminobenzoylamino)butanoic acid in 40 ml of dry methylene chloride, add 1.83 g (16.87 mmol) of trimethylsilyl chloride and allow the reaction to reflux for 5 hours. Then place the flask in an ice bath and add 1.24 g (12.33 mmol) of triethylamine and a suspension of 1.53 g (8.22 mmol) of 4-nitrobenzoyl chloride in 10 ml of dry ethyl acetate. Allow the reaction to stir for 30 minutes in an ice bath and 24 hours at room temperature. Eliminate the solvent at low pressure, add 30 ml of 10% NaOH to the crude product and continue stirring the mixture until the oil has completely disappeared. Immediately acidify with concentrated HCl, filter the resulting solid and wash several times with water and with ether. Purify the reaction product by recrystallization in dioxane/H2O . This yields 1.33 g (43%) of 4-[2-(4-nitrobenzoylamino) benzoylamino] butanoic acid as a cream-coloured solid.

Workup

  1. customthe reaction
  2. temperatureto reflux for 5 hours
  3. customthe reaction
  4. stirringcontinue stirring the mixture until the oil
  5. filtrationfilter the resulting solid
  6. washwash several times with water
  7. customPurify the reaction product
  8. customby recrystallization in dioxane/H2O

Sources & evidence

ORD record
ord-8814dd0661c14bf197e4fabd3bd46628
Source dataset
uspto-grants-2008_12
Patent number
US07462735B2

Reaction notes

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