1,3-Dichloro-5,5-dimethylhydantoin → HCID 86723405, compound

HRID 508557Notes

Reaction equation

HRID 508557 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:5]=[C:4]([CH:17]=[O:18])[CH:3]=1.[Cl:19]N1C(C)(C)C(=O)N(Cl)C1=O>CC#N>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[N:5]=[C:4]([CH:17]=[O:18])[C:3]=1[Cl:19]

Participants

4

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 86723391HCID 86723391, compound

Product 1

HCID 86723405HCID 86723405, compoundYield 136.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure for Example 15, 4-amino-5-fluoro-6-(4-fluorobenzyl)-picolinaldehyde (0.5 g, 2.014 mmol), 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.218 g, 1.108 mmol) and CH3CN (20 mL) gave 4-amino-3-chloro-5-fluoro-6-(4-fluorobenzyl)picolinaldehyde (428 mg, 73.7%) as an orange solid: mp 109-111° C.; 1H NMR (400 MHz, CDCl3) δ 10.08 (s, 1H), 7.28 (m, 3H), 6.97 (m, 2H), 4.84 (s, 2H), 4.14 (d, J=3.1 Hz, 2H); 19F NMR (376 MHz, CDCl3) δ −116.40, −139.04; 13C NMR (101 MHz, CDCl3) δ 190.27, 162.96, 160.53, 148.18, 145.80, 145.67, 145.61, 143.17, 139.85, 139.72, 133.24, 130.38, 130.31, 115.47, 115.26, 37.10, 37.08; EIMS m/z 282.

Sources & evidence

ORD record
ord-6619a2e9d6994cdc861b52c7f64f8d8f
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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