1,3-Dichloro-5,5-dimethylhydantoin → HCID 86723406, compound

HRID 508558Notes

Reaction equation

HRID 508558 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[C:4]([C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=2)[C:3]=1[F:20].[Cl:21]N1C(C)(C)C(=O)N(Cl)C1=O>CC#N>[NH2:1][C:2]1[C:7]([Cl:21])=[C:6]([CH:8]=[O:9])[N:5]=[C:4]([C:10]2[CH:11]=[N:12][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:14][CH:15]=2)[C:3]=1[F:20]

Participants

4

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 86723392HCID 86723392, compound

Product 1

HCID 86723406HCID 86723406, compoundYield 147.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure for Example 15, 4-amino-3-fluoro-6′-(trifluoromethyl)-[2,3′-bipyridine]-6-carbaldehyde (200 mg, 0.701 mmol), 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (76 mg, 0.386 mmol) and CH3CN (7 mL) gave 4-amino-5-chloro-3-fluoro-6′-(trifluoromethyl)-[2,3′-bipyridine]-6-carbaldehyde (182 mg, 69.8%) as a yellow solid: mp 147-149° C.; 1H NMR (400 MHz, CDCl3) δ 10.14 (s, 1H), 9.34 (d, J=2.0 Hz, 1H), 8.54 (m, 1H), 7.84 (m, 1H), 5.13 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −68.02, −137.62.

Sources & evidence

ORD record
ord-387619f3f03840e6a5e692a21dcfb0d4
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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