1-Hydroxybenzotriazole → 5-amino-2,4-difluoro-N-methylbenzamide

HRID 81459

Reaktionsgleichung

Reaktionsgleichung von HRID 81459
[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.[CH3:14][N:15](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CNO>C1COCC1>[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:15][CH3:14])=[O:8]

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 77906N-methylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 210494315-Amino-2,4-difluorobenzoic acid

Produkt 1

HCID 220191305-amino-2,4-difluoro-N-methylbenzamideAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-amino-2,4-difluoro-benzoic acid (6 g, 34.6 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.3 g, 69.3 mmol) and 1-hydroxybenzotriazole (9.3 g, 69.3 mmol) was stirred in THF (100 ml). Diisopropylethylamine (7.2 ml, 41.5 mmol) and methylhydroxyamine hydrochloride (4.3 g, 51.9 mmol) were added thereto, and the solution was stirred for 5 hours. The resulting solution was extracted with ethylacetate and washed with salt solution. The resulting residue was recrystallized with diethylether to obtain the title compound 5 g (yield: 71%).

Aufarbeitung

  1. extractionThe resulting solution was extracted with ethylacetate
  2. washwashed with salt solution
  3. customThe resulting residue was recrystallized with diethylether

Quellen und Nachweise

ORD-Eintrag
ord-521e82beb46b4d0d8f1480c4ab46e1cd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846699B2

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