Hydrochloric Acid → N-(3-methyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide

HRID 543570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543570
S(Cl)(Cl)=O.[CH3:5][C:6]1([C:9]([OH:11])=O)[CH2:8][CH2:7]1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH:21]([F:23])[F:22])[NH2:16].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:12][C:13]1[CH:14]=[C:15]([NH:16][C:9]([C:6]2([CH3:5])[CH2:8][CH2:7]2)=[O:11])[CH:17]=[CH:18][C:19]=1[O:20][CH:21]([F:22])[F:23]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 813261-Methylcyclopropanecarboxylic acidHCID 132950334-(Difluoromethoxy)-3-methylaniline

Produkt 1

HCID 13314709N-(3-methyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamideAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of toluene (50 ml) and pyridine (4.2 g) cooled at 0° C., thionyl chloride (1.3 g) was added, and a solution of 1-methylcyclopropanecarboxylic acid (1.0 g) in toluene was dropwise added thereto while stirring. A solution of 3-methyl-4-difluoromethoxyaniline (1.75 g) in toluene was dropwise added thereto. After the dropwise addition was completed, stirring was continued at room temperature for 3 hours. The reaction mixture was admixed with 5% hydrochloric acid (20 ml). The organic solvent layer was separated, washed with 1% sodium hydroxide solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give crude crystals (2.2 g). The crude crystals were recrystallized from ethanol to give N-(3-methyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide (1.8 g). M.P., 68°-69° C.

Aufarbeitung

  1. additionAfter the dropwise addition
  2. stirringstirring
  3. customThe organic solvent layer was separated
  4. washwashed with 1% sodium hydroxide solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give crude crystals (2.2 g)
  8. customThe crude crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9df445b6a1e14df4b8755eb4f62f3a7e
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04447260

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