Hydrochloric Acid → HCID 9904589, compound

HRID 1416395Notes

Reaction equation

HRID 1416395 reaction equation
O=C1NCNC1=O.[N+:8]([C:11]1[CH:12]=[C:13]([CH:27]=[CH:28][CH:29]=1)[CH2:14][N:15]1[C:19](=[O:20])[C:18](=O)[N:17]([CH2:22][C:23]([OH:25])=[O:24])[C:16]1=C)([O-:10])=[O:9].[OH-:30].[K+].Cl.[CH3:33]O.O>>[N+:8]([C:11]1[CH:12]=[C:13]([CH:27]=[CH:28][CH:29]=1)[CH2:14][N:15]1[C:19](=[O:20])[C:18](=[CH2:33])[N:17]([CH2:22][C:23]([OH:25])=[O:24])[C:16]1=[O:30])([O-:10])=[O:9]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10638264HCID 10638264, compoundHCID 21388926HCID 21388926, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 9904589HCID 9904589, compound

Procedure

The above-prepared dioxoimidazolidine product of paragraph (1) (241 mg) and 50.3 mg of potassium hydroxide were suspended in a mixed solution of methanol-water followed by vigorous stirring for 24 hours. The pH of the reaction mixture was adjusted to about 4 using 2N hydrochloric acid and the reaction mixture was concentrated and extracted with ethyl acetate several times. The combined extract was dried over sodium sulfate, concentrated, washed with chloroform and the insoluble matters were filtered off. The filtrate was concentrated in vacuo to give 106 mg of 3-(3-nitrobenzyl)-5-methylidene-2,4-dioxoimidazolidine-1-acetic acid [Compound 13]. The IR and NMR for the compound were:

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate several times
  3. extractionThe combined extract
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated
  6. washwashed with chloroform
  7. filtrationthe insoluble matters were filtered off
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b618a0b1cd9c45918ac741aed1b2f1f6
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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