Sodium Hydroxide → alpha-[[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]benzene acetic acid

HRID 461531Notes

Reaction equation

HRID 461531 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH2:4][N:3]1[NH:8][C:9]([NH:11][CH:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([O:15]CC)=[O:14])=[O:10].[OH-].[Na+]>>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH2:4][N:3]1[NH:8][C:9]([NH:11][CH:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([OH:15])=[O:14])=[O:10]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86734963alpha-[[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]benzeneacetic acid, ethyl ester

Product 1

HCID 20325737alpha-[[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]benzene acetic acid

Procedure

29.4 g. of α-[[[(2,4-dioxo-1-imidazolidinyl)amino]-carbonyl]amino]benzeneacetic acid, ethyl ester are added to 138 ml. of 2N sodium hydroxide solution with stirring. The substance goes quickly into solution upon slight heating. The mixture is stirred for 2 hours at room temperature, filtered and the clean filtrate is acidified to pH 1 with concentrated hydrochloric acid. Upon rubbing, α-[[[(2,4-dioxo-1-imidazolidinyl)amino]carbonyl]amino]benzene acetic acid crystallizes out. The mixture is let stand in the refrigerator overnight and then filtered under suction, yield 21.9 g., m.p. 139°-143°.

Workup

  1. filtrationfiltered
  2. customα-[[[(2,4-dioxo-1-imidazolidinyl)amino]carbonyl]amino]benzene acetic acid crystallizes out
  3. customin the refrigerator overnight
  4. filtrationfiltered under suction, yield 21.9 g

Sources & evidence

ORD record
ord-dd5cc396d0604e9c804a3197d94efd10
Source dataset
uspto-grants-1977_12
Patent number
US04063019

Reaction notes

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