1,3-Dibromo-5,5-dimethylhydantoin → HCID 86723274, compound

HRID 1846053Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:16]=[CH:15][N:14]([CH:17]([CH3:19])[CH3:18])[C:10]=3[N:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[Br:20]N1C(C)(C)C(=O)N(Br)C1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[Br:20][C:3]1[CH:4]=[C:5]([C:8]2[C:9]3[N:16]=[CH:15][N:14]([CH:17]([CH3:19])[CH3:18])[C:10]=3[N:11]=[N:12][CH:13]=2)[CH:6]=[CH:7][C:2]=1[F:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(4-fluorophenyl)-7-isopropyl-7H-imidazo[4,5-c]pyridazine (Preparation 86, 770 mg, 3.00 mmol) in concentrated sulfuric acid (7.00 mL) at 0° C. was added 1,3-dibromo-5,5-dimethyl hydantoin (687 mg, 2.40 mmol) portionwise over 1.5 hours and the reaction stirred at 0° C. for 1 hour. The reaction mixture was added dropwise into a solution of saturated aqueous sodium thiosulfate solution (20 mL) at 0° C. Following complete addition the reaction mixture was basified to pH=9 with solid potassium carbonate. The reaction mixture was filtered through celite, washed with CH2Cl2 (20 mL) and extracted into CH2Cl2 (3×40 mL), dried over Na2SO4, filtered and concentrated under vacuum to yield a pale yellow solid. Purification by silica gel column chromatography eluting with EtOAc:CH2Cl2 1:1 afforded the title compound as a pale yellow solid (558 mg, 55%).

Workup

additionaddition the reaction mixture
filtrationThe reaction mixture was filtered through celite
washwashed with CH2Cl2 (20 mL)
extractionextracted into CH2Cl2 (3×40 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customto yield a pale yellow solid
customPurification by silica gel column chromatography
washeluting with EtOAc:CH2Cl2 1:1

Sources & evidence

ORD record: ord-a2feb66809a04208b4a91a8011f1b47c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952008B2

Reaction notes

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