1,3-Dichloro-5,5-dimethylhydantoin → HCID 86723402, compound

HRID 508554Notes

Reaction equation

HRID 508554 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])[N:5]=[C:4]([CH:13]=[O:14])[CH:3]=1.[Cl:15]N1C(C)(C)C(=O)N(Cl)C1=O>>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([CH3:11])([CH3:10])[CH3:12])[N:5]=[C:4]([CH:13]=[O:14])[C:3]=1[Cl:15]

Participants

3

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 86723386HCID 86723386, compound

Product 1

HCID 86723402HCID 86723402, compoundYield 70.5%

Procedure

Using the procedure for Example 15, 4-amino-6-(tert-butyl)-5-fluoropicolinaldehyde (0.5 g, 2.55 mol), 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.276 g, 1.401 mol) CH3CN (26 mL) gave 4-amino-6-(tert-butyl)-3-chloro-5-fluoropicolinaldehyde (423 mg, 70.5%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 10.01 (s, 1H), 4.76 (d, J=7.2 Hz, 3H), 1.42 (d, J=1.6 Hz, 9H); 19F NMR (376 MHz, CDCl3) δ −132.69; 13C NMR (101 MHz, CDCl3) δ 191.27, 152.89, 149.20, 146.51, 141.75, 139.93, 36.97, 28.39; EIMS m/z 230.

Sources & evidence

ORD record
ord-fd04ca2499f14a259788ee87e4732395
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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