Triethylamine → {5-[4-Amino-6-(2-methoxy-phenylsulfanyl)-[1,3,5]triazin-2-yl]-2,4-dichlorophenoxy}-acetonitrile

HRID 217282

Reaktionsgleichung

Reaktionsgleichung von HRID 217282
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16].[NH2:17][C:18]1[N:23]=[C:22](S(CC2C=CC=CC=2)=O)[N:21]=[C:20]([C:33]2[C:34]([Cl:44])=[CH:35][C:36]([Cl:43])=[C:37]([CH:42]=2)[O:38][CH2:39][C:40]#[N:41])[N:19]=1>CN(C)C=O>[NH2:17][C:18]1[N:23]=[C:22]([S:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH3:8])[N:21]=[C:20]([C:33]2[C:34]([Cl:44])=[CH:35][C:36]([Cl:43])=[C:37]([CH:42]=2)[O:38][CH2:39][C:40]#[N:41])[N:19]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 23642ThioguaiacolHCID 57898869[5-(4-Amino-6-phenylmethanesulfinyl-[1,3,5]triazin-2-yl)-2,4-dichlorophenoxy]-acetonitrile

Produkt 1

HCID 57898818{5-[4-Amino-6-(2-methoxy-phenylsulfanyl)-[1,3,5]triazin-2-yl]-2,4-dichlorophenoxy}-acetonitrileAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Triethylamine (12 μL) and 2-methoxybenzenethiol (12 mg) were added in succession to a solution of the above-described [5-(4-amino-6-phenylmethanesulfinyl-[1,3,5]triazin-2-yl)-2,4-dichlorophenoxy]-acetonitrile (12 mg) in dimethylformamide (0.5 mL). The mixture was stirred at room temperature for 8 hours. After dilution with ethyl acetate (7 mL), the mixture was washed twice with water and once with brine. The mixture was pre-dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3) to give {5-[4-amino-6-(2-methoxy-phenylsulfanyl)-[1,3,5]triazin-2-yl]-2,4-dichlorophenoxy}-acetonitrile as white solid (10 mg).

Aufarbeitung

  1. washAfter dilution with ethyl acetate (7 mL), the mixture was washed twice with water and once with brine
  2. dry with materialThe mixture was pre-dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationThe solvent was distilled off
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=7:3)

Quellen und Nachweise

ORD-Eintrag
ord-ef965fb2a051411791d949e5a75fcaf6
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193351B2

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