1,3-Dibromo-5,5-dimethylhydantoin → Diethyl dioxobutanedioate

HRID 1028480Notes

Reaction equation

HRID 1028480 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C@@H:5]([C@H:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[OH:8])[OH:6])[CH3:2].BrN1C(C)(C)C(=O)N(Br)C1=O.N(C(C)(CC(OC)(C)C)C#N)=NC(C)(CC(C)(OC)C)C#N>C(O)(=O)C>[O:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:14])[C:7](=[O:8])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 6993580Diethyl tartrate

Product 1

HCID 263091Diethyl dioxobutanedioate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

L-Tartaric acid diethyl ester (50.0 g), acetic acid (900 ml), 1,3-dibromo-5,5-dimethylhydantoin (149.1 g) and 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (750 mg) were mixed, and the reaction solution was stirred at 70° C. for 2 hours, followed by stirring at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure until its volume became approximately 300 ml to obtain a solution of diethyl dioxobutanedioate in acetic acid as a yellow liquid.

Workup

  1. stirringby stirring at room temperature for 16 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure until its volume

Sources & evidence

ORD record
ord-cb9051777f8c4d99ba539b882e01d1ef
Source dataset
uspto-grants-2014_05
Patent number
US08735598B2

Reaction notes

Loading…