1,3-Dichloro-5,5-dimethylhydantoin → 4-((3-Chloro-6-(4-chlorophenyl)-2-(diethoxymethyl)-5-fluoropyridin-4-yl)imino)cyclohexa-2,5-dienone

HRID 1503105Notes

Reaction equation

HRID 1503105 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([F:14])=[C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=3)[CH:11]=[C:10]([CH:24]([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])[N:9]=2)=[CH:4][CH:3]=1.[Cl:31]N1C(C)(C)C(=O)N(Cl)C1=O>C(#N)C.O>[Cl:31][C:11]1[C:10]([CH:24]([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])=[N:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:13]([F:14])[C:12]=1[N:15]=[C:16]1[CH:21]=[CH:20][C:19](=[O:22])[CH:18]=[CH:17]1

Participants

4

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 867233522-(4-chlorophenyl)-6-(diethoxymethyl)-3-fluoro-N-(4-methoxyphenyl)pyridin-4-amine

Product 1

HCID 867233544-((3-Chloro-6-(4-chlorophenyl)-2-(diethoxymethyl)-5-fluoropyridin-4-yl)imino)cyclohexa-2,5-dienoneYield 30.3%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 2-(4-chlorophenyl)-6-(diethoxymethyl)-3-fluoro-N-(4-methoxy-phenyl)pyridin-4-amine (0.862 g, 2 mmol) and 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.788 g, 4.00 mmol) in 1:1 acetonitrile/water (20 mL) was stirred at room temperature. After 2 h, the orange solid was collected by filtration, washed with 1:1 acetonitrile/water (5 mL), dried at room temperature and recrystallized from ether/hexane. 4-((3-Chloro-6-(4-chlorophenyl)-2-(diethoxymethyl)-5-fluoropyridin-4-yl)imino)cyclohexa-2,5-dienone (0.272 g, 30% yield) was isolated as orange crystals: mp 134-136° C.; 1H NMR (400 MHz, CDCl3) δ 7.96 (m, 2H), 7.44 (m, 3H), 6.76 (m, 2H), 6.58 (dd, J=10.2, 2.1 Hz, 1H), 5.79 (s, 1H), 3.90 (m, 2H), 3.72 (m, 2H), 1.31 (t, J=7.1 Hz, 6H); 19F NMR (376 MHz, CDCl3) δ −134.18; HRMS-ESI (m/z) [M+H]+ calcd for C22H19Cl2FN2O3, 448.0757; found, 448.0761.

Workup

  1. filtrationthe orange solid was collected by filtration
  2. washwashed with 1:1 acetonitrile/water (5 mL)
  3. customdried at room temperature
  4. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-75a8b867751c408b9b4c33fda70c4a0b
Source dataset
uspto-grants-2015_12
Patent number
US09212141B2

Reaction notes

Loading…