Sulfuric Acid → Methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate

HRID 1774284ノート

反応式

HRID 1774284 の反応式
COC1C=CC([NH:9][C:10]2[C:15]([F:16])=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:13]=[C:12]([C:24]([O:26][CH3:27])=[O:25])[CH:11]=2)=CC=1.[Cl:28]N1C(C)(C)C(=O)N(Cl)C1=O.S(=O)(=O)(O)O.C(Cl)Cl>C(#N)C.O>[NH2:9][C:10]1[C:15]([F:16])=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:13]=[C:12]([C:24]([O:26][CH3:27])=[O:25])[C:11]=1[Cl:28]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 86723349Methyl 4-(4-methoxyphenylamino)-5-fluoro-6-(4-chlorophenyl)picolinate

生成物 1

HCID 22677303Methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate

試薬・触媒・溶媒 1

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

実験手順

In a typical reaction accomplishing both chlorination and deprotection, methyl 4-(4-methoxyphenylamino)-5-fluoro-6-(4-chlorophenyl)picolinate is reacted with about two equivalents of 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione in the presence of a 1 M (molar) solution of sulfuric acid in a mixture of acetonitrile/water. The mixture is heated at reflux until the reaction is complete. The mixture is added to methylene chloride and the organic layer is separated, washed with brine and dried. The solvent is evaporated to provide crude methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate.

後処理

  1. customIn a typical reaction
  2. temperatureThe mixture is heated
  3. temperatureat reflux until the reaction
  4. customthe organic layer is separated
  5. washwashed with brine
  6. customdried
  7. customThe solvent is evaporated

出典と根拠

ORDレコード
ord-e9c59ea5d0594784b7fa0121174f2fcd
出典データセット
uspto-grants-2016_02
特許番号
US09260392B2

反応ノート

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