Glyoxylic Acid → 1-Benzyl-5-hydroxyimidazolidine-2,4-dione

HRID 840390Notes

Reaction equation

[C:1]([OH:5])(=O)[CH:2]=[O:3].[CH2:6]([NH:13][C:14]([NH2:16])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>C(O)(=O)C>[CH2:6]([N:13]1[CH:1]([OH:5])[C:2](=[O:3])[NH:16][C:14]1=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3000 parts by weight of 50% strength aqueous glyoxylic acid solution and 500 parts by weight of acetic acid (100% strength) are placed in a heatable, stirred apparatus and heated to 100° C. A mixture of 3000 parts by weight of benzylurea, 1300 parts by weight of water and 1500 parts by weight of acetic acid having a temperature of 80° C. is added to this solution over a period of one hour. The total reaction mixture is subsequently stirred at an internal temperature of 100° C. for another hour. 4500 parts by weight of an acetic acid/water mixture are then distilled off to a pressure of 200 mbar and a temperature at the bottom of 100° C. The remaining liquid residue is admixed at 90° C. with 900 parts by weight of water and 12.5 parts by weight of acetic acid, cooled to 35° C., admixed with 3000 parts by weight of methylene chloride and stirred at 25° C. for 12 hours. The temperature is then held at 3° C. for 1 hour by cooling.

Workup

additionis added to this solution over a period of one hour
customThe total reaction mixture
stirringis subsequently stirred at an internal temperature of 100° C. for another hour
distillation4500 parts by weight of an acetic acid/water mixture are then distilled off to a pressure of 200 mbar
custombottom of 100° C
customis admixed at 90° C. with 900 parts by weight of water and 12.5 parts by weight of acetic acid
temperaturecooled to 35° C.
stirringstirred at 25° C. for 12 hours
temperatureby cooling

Sources & evidence

ORD record: ord-3dd9a5840a11419099920d708946ecc8
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365752B1

Reaction notes

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