Hydrogen Bromide → 3-Bromomethyl-1,5,5-trimethylhydantoin

HRID 565802Notes

Reaction equation

HRID 565802 reaction equation
[CH3:1][N:2]1[C:8]([CH3:10])([CH3:9])[C:6](=O)[NH:5][C:3]1=[O:4].[CH2:11]=[O:12].[BrH:13]>C(O)(=O)C.C(Cl)Cl>[Br:13][CH2:6][N:5]1[C:11](=[O:12])[C:8]([CH3:10])([CH3:9])[N:2]([CH3:1])[C:3]1=[O:4]

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 712FormaldehydeHCID 812951,5,5-Trimethylimidazolidine-2,4-dione

Product 1

HCID 109334353-Bromomethyl-1,5,5-trimethylhydantoinYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of 21.3 g of 1,5,5-trimethylhydantoin, 5.86 g of paraformaldehyde and 34 ml of hydrogen bromide in acetic acid (33%) was heated to 800 for 2 hrs., again treated with 7.9 ml of hydrogen bromide in acetic acid and heated for a further 2.5 hrs. The solution was cooled to 0°, diluted with 100 ml of methylene chloride and subsequently treated at 0° with 100 ml of ice-cold water. The methylene chloride phase was washed with water, dried and concentrated. The residue was crystallized from t-butyl methyl ether/hexane and the crystallizate was dried, there being obtained 30.9 g (88%) of pure 3-bromomethyl-1,5,5-trimethylhydantoin, m.p. 86-88°. IR (KBr): 1780s and 1732s (C═O).

Workup

  1. temperaturewas heated to 800 for 2 hrs
  2. temperatureheated for a further 2.5 hrs
  3. temperatureThe solution was cooled to 0°
  4. washThe methylene chloride phase was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was crystallized from t-butyl methyl ether/hexane
  8. customthe crystallizate was dried

Sources & evidence

ORD record
ord-80b3d8c67a8c4def93bbc20024e07f6a
Source dataset
uspto-grants-2001_01
Patent number
US06172238B2

Reaction notes

Loading…