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

HRID 1774284노트

반응식

HRID 1774284 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9c59ea5d0594784b7fa0121174f2fcd
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260392B2

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