1,3-Dibromo-5,5-dimethylhydantoin → HCID 15547193, compound

HRID 2084038Notes

Reaction equation

HRID 2084038 reaction equation
[CH2:1]([N:8]1[C:18]2=[C:19]3C(=[CH:15][CH:16]=[CH:17]2)C=C[CH2:11][N:10]3[C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H+].[B-](F)(F)(F)F.CC1(C)N([Br:35])C(=O)N(Br)C1=O.[C:38]([O:42]C)([CH3:41])([CH3:40])C>C(#N)C.O>[CH2:1]([N:8]1[C:18]2=[C:19]3[C:40](=[CH:15][CH:16]=[CH:17]2)[C@@H:38]([OH:42])[C@H:41]([Br:35])[CH2:11][N:10]3[C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 15413tert-Butyl methyl etherHCID 28118Tetrafluoroboric acidHCID 97952141-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Product 1

HCID 15547193HCID 15547193, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

1-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (II, EXAMPLE 1, 240 g), acetonitrile (1.086 kg), water (227 ml) and fluoboric acid (48.5%, 13.4 g) are mixed and cooled to 0 to 5°. Dibromantin (163.5 g) is slurried into acetonitrile and is added to the reaction mixture. The reaction is carried out for about 3 hr at 0 to 5°. After the reaction is complete, methyl t-butyl ether is added over about 45 minutes keeping the reaction temperature in the pot below 10°. The slurry is cooled to −10 to −15°, stirred for an hour and then filtered. The product is washed with precooled methyl t-butyl ether, dried with 40° nitrogen to give the title compound, CMR (CDCl3) 156.0, 137.8, 130.5, 129.6, 129.3, 129.1, 126.6, 123.6, 122.5, 119.6, 110.4, 69.9, 49.6, 47.7, 46.9 and 43.8 δ.

Workup

  1. temperaturecooled to 0 to 5°
  2. additionis added to the reaction mixture
  3. customin the pot below 10°
  4. temperatureThe slurry is cooled to −10 to −15°
  5. filtrationfiltered
  6. washThe product is washed with precooled methyl t-butyl ether
  7. customdried with 40° nitrogen

Sources & evidence

ORD record
ord-e39548082ce54e8dad54d7805cdc0867
Source dataset
uspto-grants-2004_04
Patent number
US06716854B2

Reaction notes

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