1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529885, compound

HRID 1972795Notes

Reaction equation

HRID 1972795 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH2:17][OH:18])[CH:14]=[CH:15][CH:16]=3)[N:6]2[N:5]=[CH:4][N:3]=1.C1COCC1.[Br:24]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])=O.[Na+].[Na+].O>[NH2:1][C:2]1[C:7]2=[C:8]([Br:24])[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH2:17][OH:18])[CH:14]=[CH:15][CH:16]=3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 8028TetrahydrofuranHCID 58529804HCID 58529804, compound

Product 1

HCID 58529885HCID 58529885, compoundYield 191.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolventHCID 24437Sodium SulfiteSolvent

Procedure

The product from step 1 (1.54 g, 6.4 mmol) was dissolved in 18 mL of 1:1 DMF:THF. The mixture was cooled to −20° C. (internal temperature) and 1,3-dibromo-5,5-dimethylhydantoin (0.92 g, 3.2 mmol) was added in 4 equal portions over 40 minutes. The mixture was stirred for an additional 1 hour during which the internal temp rose to −5° C. A solid mass formed, which was diluted with a mixture of 15 mL of 2M Na2CO3, 10 mL of sat. Na2SO3 and 60 mL of water and the mixture was stirred for an additional 30 minutes. The solid was collected by filtration, washed with water and dried in a vacuum oven at 40° C. to give 1.96 g (95%) of the title compound as a tan solid. 1H-NMR (DMSO-d6) 8.10 (bs, 1H), 7.94 (s, 2H), 7.86 (d, 1H), 7.40 (t, 1H), 7.29 (d, 1H), 7.17 (s, 1H), 6.84 (bs, 1H), 5.22 (t, 1H), 4.56 (d, 2H); LC-MS [M+H]+=319.3, 321.1, RT=2.29 min.

Workup

  1. additionwas added in 4 equal portions over 40 minutes
  2. customrose to −5° C
  3. customA solid mass formed
  4. stirringthe mixture was stirred for an additional 30 minutes
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-00171d267d4f474a9657468a660d31e5
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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