1,3-Dichloro-5,5-dimethylhydantoin → HCID 86723403, compound

HRID 508555Notes

Reaction equation

HRID 508555 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH:10]2[CH2:12][CH2:11]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]([CH2:9][CH:10]2[CH2:12][CH2:11]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 86723387HCID 86723387, compound

Product 1

HCID 86723403HCID 86723403, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure for Example 15, 4-amino-6-(cyclopropylmethyl)-5-fluoropicolinaldehyde (0.5 g, 2.57 mmol), 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.279 g, 1.416 mmol) and CH3CN (26 mL) gave 4-amino-3-chloro-6-(cyclopropylmethyl)-5-fluoropicolinaldehyde (138 mg, 0.604 mmol, 23.44%) as an orange oil: 1H NMR (400 MHz, CDCl3) δ 10.09 (s, 1H), 4.83 (s, 3H), 2.75 (dd, J=7.0, 2.8 Hz, 3H), 1.26 (t, J=7.1 Hz, 1H), 0.50 (m, 3H), 0.28 (dt, J=6.2, 4.6 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −139.49; 13C NMR (101 MHz, CDCl3) δ 190.47, 148.35, 147.05, 145.79, 143.11, 139.40, 116.45, 36.23, 10.04, 4.51.

Sources & evidence

ORD record
ord-91e845a0f7f943bdac09e0fcc6fcc811
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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