Hydrochloric Acid → 3-[4-(4-Cyanobenzamidomethyl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid

HRID 977223Notes

Reaction equation

HRID 977223 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[O:11][C:10]2=[O:17])=[CH:5][CH:4]=1.[OH-].[Na+].[C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)#[N:21].Cl>C1COCC1>[C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([N:9]3[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[O:11][C:10]3=[O:17])=[CH:7][CH:8]=2)=[O:27])=[CH:24][CH:23]=1)#[N:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 801724-Cyanobenzoyl chlorideHCID 199655363-(4-Aminomethylphenyl)-2-oxo-5-oxazolidinecarboxylic acid

Product 1

HCID 199655393-[4-(4-Cyanobenzamidomethyl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.4 g of 3-(4-aminomethylphenyl)-2-oxo-5-oxazolidinecarboxylic acid are suspended in 70 ml of THF. 35 ml of 1N NaOH are added dropwise with stirring. Subsequently, a solution of 6.6 g of 4-cyanobenzoyl chloride in 60 ml of THF is added dropwise. The pH of the solution is maintained at between 9 and 10.5 by addition of 1N NaOH. After reaction has taken place, the mixture is acidified at a pH of 1 with 2N HCl. The solvent is removed and the residue is filtered off with suction and washed with water. 3-[4-(4-cyanobenzamidomethyl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid is obtained, m.p. 234°.

Workup

  1. customAfter reaction
  2. customThe solvent is removed
  3. filtrationthe residue is filtered off with suction
  4. washwashed with water

Sources & evidence

ORD record
ord-1021e66a4356448eb3a4028775bbcc0d
Source dataset
uspto-grants-1997_03
Patent number
US05614535

Reaction notes

Loading…