1-Aminohydantoin → alpha-[[[(2,4-Dioxo-1-imidazolidinyl)amino]carbonyl]amino]benzeneacetic acid, ethyl ester

HRID 259390Notes

Reaction equation

HRID 259390 reaction equation
[NH2:1][N:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[N:9]([CH:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]=[O:11]>O1CCOCC1>[O:8]=[C:3]1[NH:4][C:5](=[O:7])[CH2:6][N:2]1[NH:1][C:10]([NH:9][CH:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:11]

Participants

4

Reactant 2

HCID 728231-AminohydantoinHCID 56982438alpha-Isocyanatobenzeneacetic acid, ethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.15 g. (0.01 mol.) of 1-amino-2,4-dioxoimidazolidine are dissolved in 50 ml. of dioxane while heating. The solution is permitted to cool to room temperature while stirring, wherein a portion of the 1-amino-2,4-dioxoimidazolidine crystallizes out. 2.05 g. (0.01 mol.) of α-isocyanatobenzeneacetic acid, ethyl ester are added and the reation mixture is stirred overnight at room temperature. On the next day the mixture is concentrated and the residue is triturated with ether. 3.0 g. of α-[[[(2,4-dioxo-1-imidazolidinyl)amino]-carbonyl] amino]benzeneacetic acid, ethyl ester are obtained, m.p. 148°-151°.

Workup

  1. customwherein a portion of the 1-amino-2,4-dioxoimidazolidine crystallizes out
  2. stirringthe reation mixture is stirred overnight at room temperature
  3. concentrationOn the next day the mixture is concentrated
  4. customthe residue is triturated with ether

Sources & evidence

ORD record
ord-5135711ffbba467f97cb00c6db5a74f4
Source dataset
uspto-grants-1977_07
Patent number
US04038271

Reaction notes

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