1,3-Dibromo-5,5-dimethylhydantoin → HCID 14563110, compound

HRID 1089540Notes

Reaction equation

HRID 1089540 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[O:18][CH3:19])[C:8](=[O:20])[C:7]=2[CH:6]=[C:5]([CH3:21])[CH:4]=1.[Br:22]N1C(C)(C)C(=O)N(Br)C1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:21][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:16]2[C:15](=[O:17])[C:14]3[C:9]([C:8](=[O:20])[C:7]=2[CH:6]=1)=[CH:10][CH:11]=[CH:12][C:13]=3[O:18][CH3:19]

Participants

5

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7187Benzoyl PeroxideHCID 189763Chrysophanol dimethyl ether

Product 1

HCID 14563110HCID 14563110, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a hot solution of 1,8-dimethoxy-3-methyl-9,10-anthraquinone (4.5 g, 16 mM) and 1,3-dibromo-5,5-dimethylhydantoin (2.75 g, 19.2 mM) in carbon tetrachloride (500 mL) is added benzoyl peroxide (0.7 g), and the mixture is heated under reflux for 5 hours. The mixture is allowed to cool to room temperature. Insoluble hydantoin is removed by filtration, the filtrate is concentrated to dryness, and the residue recrystallized twice from ethyl acetate to give 3-bromomethyl-1,8-dimethoxy-9,10-anthraquinone (3.3 g, 57%), mp 176-178° C. 1H NMR (CDCl3) δ: 4.01 (3H, s, OMe), 4.03 (3H, s, OMe), 4.52 (2H, s, CH2Br), 7.26-7.84 (5H, m, aromatic H). Analyses (C17H13BrO4). Calculated: C, 56.53; H, 3.63; Br, 22.12. Found: C, 56.48; H, 3.67; Br, 21.93.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 hours
  3. customInsoluble hydantoin is removed by filtration
  4. concentrationthe filtrate is concentrated to dryness
  5. customthe residue recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-f5619eb70196410898118fe2bd7c11d9
Source dataset
uspto-grants-1990_10
Patent number
US04966918

Reaction notes

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