Hydrochloric Acid → HCID 19912213、化合物

HRID 1090988ノート

反応式

HRID 1090988 の反応式
[Cl:1][C:2]1[CH:18]=[C:17]([F:19])[C:16]([N:20]2[C:24](=[O:25])[N:23]([CH:26]([F:28])[F:27])[C:22]([CH3:29])=[N:21]2)=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([O:13]C)=[O:12])=[CH:7][CH:6]=1.ClC1C=C(F)C(N2C(=O)N(C(F)F)C(C)=N2)=CC=1OC1C=CC(C(OCC)=O)=CC=1.[OH-].[Na+].Cl>O1CCCC1.O.C(O)C>[Cl:1][C:2]1[CH:18]=[C:17]([F:19])[C:16]([N:20]2[C:24](=[O:25])[N:23]([CH:26]([F:28])[F:27])[C:22]([CH3:29])=[N:21]2)=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19912204methyl 4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]-phenylcarboxylateHCID 19912232ethyl 4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]phenylcarboxylate

生成物 1

HCID 19912213HCID 19912213、化合物収率 143.9%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a stirred mixture of 1.8 g (0.0042 mole) of methyl 4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4 -triazol-1-yl)phenoxy]-phenylcarboxylate and 1.3 g (0.0029 mole) of ethyl 4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro -3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]phenylcarboxylate (prepared by the method of Step B using ethanol in place of methanol) in 20 mL of tetrahydrofuran was added a solution of 0.58 g (0.014) of sodium hydroxide in 30 mL of water. The reaction mixture was heated at 50° C. for 1.5 hour, then was stirred at room temperature for approximately 18 hours. The mixture was again heated at 50° C. for two hours and then was allowed to cool. The solvent was removed from the mixture by evaporation under reduced pressure leaving a residue. The residue was stirred in a 2N hydrochloric acid solution, and the resultant mixture was extracted successively with diethyl ether and ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a solid residue. The residue was purified by column chromatography on silica gel, eluting with methylene chloride:methanol (95:5) to give 2.5 g of 4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo 1H-1,2,4-triazol-1-yl)phenoxy]phenylcarboxylic acid as a solid, m.p. 184°-185° C.

後処理

  1. customprepared by the method of Step B
  2. temperatureThe mixture was again heated at 50° C. for two hours
  3. temperatureto cool
  4. customThe solvent was removed from the mixture by evaporation under reduced pressure
  5. customleaving a residue
  6. extractionthe resultant mixture was extracted successively with diethyl ether and ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure
  10. customto give a solid residue
  11. customThe residue was purified by column chromatography on silica gel
  12. washeluting with methylene chloride:methanol (95:5)

出典と根拠

ORDレコード
ord-daa531dfd6ac4faeb71c8feb4057292b
出典データセット
uspto-grants-1992_01
特許番号
US05084085

反応ノート

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