1,3-Dichloro-5,5-dimethylhydantoin → HCID 86723407, compound

HRID 508559Notes

Reaction equation

HRID 508559 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH:9]2[CH2:13][CH2:12][CH2:11][O:10]2)[N:5]=[C:4]([CH:14]=[O:15])[CH:3]=1.[Cl:16]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[CH2:13][CH2:12][CH2:11][O:10]2)[N:5]=[C:4]([CH:14]=[O:15])[C:3]=1[Cl:16]

Participants

4

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 86723396HCID 86723396, compound

Product 1

HCID 86723407HCID 86723407, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure for Example 15, 4-amino-5-fluoro-6-(tetrahydrofuran-2-yl)picolinaldehyde (0.5 g, 2.379 mmol), 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.258 g, 1.308 mmol) and CH3CN (24 mL) gave 4-amino-3-chloro-5-fluoro-6-(tetrahydrofuran-2-yl)picolinaldehyde (59 mg, 10.14%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 10.04 (m, 1H), 5.24 (td, J=7.0, 1.7 Hz, 1H), 4.86 (d, J=9.6 Hz, 2H), 4.11 (m, 1H), 3.98 (td, J=7.8, 5.6 Hz, 1H), 2.30 (m, 2H), 1.26 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −140.28; 13C NMR (101 MHz, CDCl3) δ 190.69, 148.31, 146.23, 145.56, 143.05, 139.88, 75.77, 69.34, 30.51, 26.31; EIMS m/z 243.

Sources & evidence

ORD record
ord-df627e10f8f34d7db2b77fe9ec9b1ebb
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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