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Chloroacetyl chloride → 2-Chloro-N-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide

HRID 1760674
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1760674
C(C([C:6]1[C:7]([NH2:24])=[C:8]([NH2:23])[C:9]([O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])=[N:10][C:11]=1[CH3:12])CC)C.[Cl:25][CH2:26][C:27](Cl)=[O:28].C(N([CH2:35][CH3:36])CC)C.[CH2:37]1[CH2:41]OC[CH2:38]1>>[Cl:25][CH2:26][C:27]([NH:23][C:8]1[C:9]([O:13][C:14]2[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])=[N:10][C:11]([CH3:12])=[CH:6][C:7]=1[NH:24][CH:38]([CH2:35][CH3:36])[CH2:37][CH3:41])=[O:28]
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Komponenten

5

Edukt 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 867595891-Ethyl-propyl-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine

Produkt 1

HCID 120183492-Chloro-N-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide

Versuchsvorschrift

To a solution of N+(1-ethyl-propyl-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine (250 mg, 0.763 mmol) in dry THF was added chloroacetyl chloride (86 mg, 0.763 mmol) and triethylamine (77 mg, 0.763 mmol) at 0° C. The resulting mixture was warmed to room temperature and stirred for 1 hr. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound as a solid. The solid was purified through silica gel column chromatography to give 280 mg(91%) of tan crystals, mp. 152-154° C.

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9f338a7e454747798e66212fc63edc6f
Quelldatensatz
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06844351B1

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