Hydrochloric Acid → HCID 23118567, compound

HRID 2374710Notes

Reaction equation

HRID 2374710 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5].C[Si](Cl)(C)C.C(N(CC)CC)C.C([O:30][C:31]1[C:32](=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:33](Cl)=[O:34])(=O)C.[OH-].[Na+].Cl>C(Cl)Cl>[OH:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])=[O:34]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 796682-Acetoxybenzoyl chlorideHCID 30805622-Aminohippuric acid

Product 1

HCID 23118567HCID 23118567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4.74 g (24.44 mmol) of 2-(2-aminobenzoylamino)ethanoic acid in 40 ml of dry methylene chloride, add 5.05 g (4.28 mmol) of trimethylsilyl chloride and allow the reaction to reflux for 5 hours. Then place the flask in an ice bath and add 3.16 g (31.32 mmol) of triethylamine and a solution of 4.13 g (20.88 mmol) of acetylsalicyloyl chloride dissolved in 10 ml of dry methylene chloride. 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 40 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 (EtOH/H2O). This yields 3.54 g (54%) of 2-[2-(2-hydroxybenzoylamino) benzoylamino]ethanoic acid as a white 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 (EtOH/H2O)

Sources & evidence

ORD record
ord-bf3cde7bff914a5aa83557121eb38560
Source dataset
uspto-grants-2008_12
Patent number
US07462735B2

Reaction notes

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