Dichloroacetyl chloride → 2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)-N-(isopropoxymethyl)acetamide

HRID 1782189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1782189
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([NH:20][CH2:21][O:22][CH:23]([CH3:25])[CH3:24])[CH:17]=[CH:16][N:15]=2)[O:11][N:10]=1.C(N(CC)CC)C.[Cl:33][CH:34]([Cl:38])[C:35](Cl)=[O:36]>ClCCl>[Cl:33][CH:34]([Cl:38])[C:35]([N:20]([C:18]1[CH:17]=[CH:16][N:15]=[C:14]([C:12]2[O:11][N:10]=[C:9]([C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:13]=2)[CH:19]=1)[CH2:21][O:22][CH:23]([CH3:25])[CH3:24])=[O:36]

Komponenten

5

Edukt 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 575884942-(3-(2,6-dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine

Produkt 1

HCID 575883132,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)-N-(isopropoxymethyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(3-(2,6-Dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine (269 mg, 0.58 mmol) was dissolved in anhydrous dichloromethane with triethylamine (100 μL, 0.70 mmol). The mixture was cooled in an ice-bath under nitrogen, then a solution of dichloroacetyl chloride (70 μL, 0.70 mmol) was added dropwise. After the addition was completed the ice-bath was removed and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and then washed successively with water, 10% hydrochloric acid and saturated sodium bicarbonate solution. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography, on silica gel, eluting with 99:1 dichloromethane:methanol to yield 2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)-N-(isopropoxymethyl)acetamide (Cpd. No. 4). 1H NMR (CDCl3): 8.81 (d, 1H), 8.02 (s, 1H), 7.51-7.32 (m, 3H), 7.12 (s, 1H), 6.23 (s, 1H), 5.21 (s, 2H), 6.00 (s, 1H), 3.90 (m, 1H), 3.10 ppm (m, 6H). MW=489 confirmed by LC-MS, tr=14.57 min (Method Y) MH+=487-491.

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice-bath under nitrogen
  2. additionAfter the addition
  3. customwas removed
  4. additionThe reaction mixture was diluted with dichloromethane
  5. washwashed successively with water, 10% hydrochloric acid and saturated sodium bicarbonate solution
  6. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by flash column chromatography, on silica gel
  10. washeluting with 99:1 dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3f98f37c0f544b6aa3af9b7554f1742b
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498353B2

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