Propionic Acid → Flumiclorac-pentyl

HRID 704471

反応式

HRID 704471 の反応式
[Cl:1][C:2]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:12])=[CH:7][C:5]([NH2:6])=[C:4]([F:19])[CH:3]=1.[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2[CH2:26][CH2:27][CH2:28][CH2:29][C:21]1=2.C(O)(=O)CC.C1(C)C=CC=CC=1>N1CCCCC1.O>[Cl:1][C:2]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:12])=[CH:7][C:5]([N:6]2[C:23](=[O:24])[C:22]3[CH2:26][CH2:27][CH2:28][CH2:29][C:21]=3[C:20]2=[O:25])=[C:4]([F:19])[CH:3]=1

参加物

7

反応物 4

HCID 1032Propionic AcidHCID 1140TolueneHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 146178504-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)aniline

生成物 1

HCID 443048Flumiclorac-pentyl収率 91.7%

試薬・触媒・溶媒 2

HCID 8082Piperidine触媒HCID 962Water溶媒

実験手順

A mixture of the compound (II) (12.0 g), 3,4,5,6-tetrahydrophthalic anhydride (7.56 g), piperidine (0.18 g), propionic acid (0.30 g) and toluene (24 g) was heated under reflux for 5 hours, during which water as by-produced was azeotropically removed. To the reaction mixture, toluene (24 g) and water (24 g) were added, and the organic layer was separated and concentrated under reduced pressure. To the residue, water (18 g) and methanol (33 g) were added, and the precipitated crystals were collected by filtration to give N-[4-chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide (Compound (I)) (16.1 g). By the use of a high speed liquid chromatography, the purity of the compound (I) as the major product and the amount of the by-produced 4-chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)acetanilide (hereinafter referred to as "N-acetyl compound") as a contaminant were determined according to the inner standard method and the area comparison method, respectively.

後処理

  1. temperaturewas heated
  2. customas by-produced
  3. customwas azeotropically removed
  4. additionTo the reaction mixture, toluene (24 g) and water (24 g) were added
  5. customthe organic layer was separated
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue, water (18 g) and methanol (33 g) were added
  8. filtrationthe precipitated crystals were collected by filtration

出典と根拠

ORDレコード
ord-3637325cad1343d794afc80ea7b2a3ca
出典データセット
uspto-grants-1991_01
特許番号
US04987247

関連ノート

読み込み中…