1,3-Dichloro-5,5-dimethylhydantoin → HCID 86723404, compound

HRID 508556Notes

Reaction equation

HRID 508556 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH:9]2[CH2:12][CH2:11][CH2:10]2)[N:5]=[C:4]([CH:13]=[O:14])[CH:3]=1.[Cl:15]N1C(C)(C)C(=O)N(Cl)C1=O>CC#N>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH:9]2[CH2:12][CH2:11][CH2:10]2)[N:5]=[C:4]([CH:13]=[O:14])[C:3]=1[Cl:15]

Participants

4

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 86723389HCID 86723389, compound

Product 1

HCID 86723404HCID 86723404, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure for Example 15, 4-amino-6-cyclobutyl-5-fluoropicolinaldehyde (0.5 g, 2.57 mol), 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.279 g, 1.416 mol) and CH3CN (26 mL) gave 4-amino-3-chloro-6-cyclobutyl-5-fluoropicolinaldehyde (289 mg, 45.7%) as a red foam: 1H NMR (400 MHz, CDCl3) δ 10.09 (s, 1H), 4.77 (d, J=9.4 Hz, 2H), 3.87 (ttdd, J=9.3, 8.3, 2.3, 1.1 Hz, 2H), 2.49 (m, 2H), 2.30 (m, 2H), 2.10 (m, 1H), 1.95 (tddd, J=13.4, 7.1, 3.5, 2.1 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −140.24; 13C NMR (101 MHz, CDCl3) δ 191.04, 149.06, 147.71, 145.14, 142.84, 139.20, 115.84, 35.24, 26.86, 18.62; EIMS m/z 228.

Sources & evidence

ORD record
ord-6b6b3ba332194665a421c641d8cedc44
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

Loading…