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

HRID 1503102Notes

Reaction equation

HRID 1503102 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-dienone

Reagents, catalysts & solvents 1

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

Procedure

In a typical reaction, crude 2-(4-chlorophenyl)-6-(diethoxymethyl)-3-fluoro-N-(4-methoxyphenyl)pyridin-4-amine is treated with two equivalents of 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione in an acetonitrile/water mixture. The mixture is stirred at ambient temperature until the reaction is complete. The solid product is collected by filtration, washed with additional acetonitrile/water mixture and dried, providing crude 4-((3-chloro-6-(4-chlorophenyl)-2-(diethoxymethyl)-5-fluoropyridin-4-yl)imino)cyclohexa-2,5-dienone.

Workup

  1. filtrationThe solid product is collected by filtration
  2. washwashed with additional acetonitrile/water mixture
  3. customdried

Sources & evidence

ORD record
ord-79ec7235a00241d3b45d331c7ad46ce4
Source dataset
uspto-grants-2015_12
Patent number
US09212141B2

Reaction notes

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