1,3-Dibromo-5,5-dimethylhydantoin → HCID 54746388, compound

HRID 602433Notes

Reaction equation

HRID 602433 reaction equation
[Br:1]N1C(C)(C)C(=O)N(Br)C1=O.[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[N:16]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=2[CH3:30])[C:23]([O:25][CH3:26])=[O:24])[C:15](=[O:31])[CH:14]=1>C(#N)C>[Br:1][C:14]1[C:15](=[O:31])[N:16]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=2[CH3:30])[C:23]([O:25][CH3:26])=[O:24])[C:17]([CH3:19])=[CH:18][C:13]=1[OH:12]

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 54724193methyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate

Product 1

HCID 54746388HCID 54746388, compoundYield 171.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 1,3-dibromo-5,5-dimethylhydantoin (1.375 kg. 4.81 moles) in acetonitrile (11.5 L) was added to a solution of methyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate (5) (2.50 kg, 9.15 mol) in acetonitrile (4.8 L). The solution was added at a rate that maintained the temperature less than −10° C. for 90 to 180 minutes. A portion of the acetonitrile (approximately 6 L) was removed after completion of the reaction via distillation. The product was precipitated by the addition of water (7.9 L) and filtered to yield 2.90 kg (90%) of methyl 3-(3-bromo-4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate (4)

Workup

  1. additionThe solution was added at a rate that
  2. temperaturemaintained the temperature less than −10° C. for 90 to 180 minutes
  3. customA portion of the acetonitrile (approximately 6 L) was removed
  4. customafter completion of the reaction
  5. distillationvia distillation
  6. customThe product was precipitated by the addition of water (7.9 L)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e4404e1992ce45a9a7078202cad90f3d
Source dataset
uspto-grants-2011_03
Patent number
US07906536B2

Reaction notes

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