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Pyridine → [4-(2,6-dichlorophenyl)-1,2,5-thiadiazol-3-yl] N-(2-cyanoethyl)-N-methyl-carbamate

HRID 617446
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 617446
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([OH:14])=[N:12][S:11][N:10]=1.[C:15](=[O:26])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.N1C=CC=CC=1.[C:33]([CH2:35][CH2:36][NH:37][CH3:38])#[N:34]>ClCCl.O>[CH3:38][N:37]([C:15]([O:14][C:13]1[C:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[N:10][S:11][N:12]=1)=[O:26])[CH2:36][CH2:35][C:33]#[N:34]
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Komponenten

7

Edukt 4

HCID 1049PyridineHCID 69656Propanenitrile, 3-(methylamino)-HCID 94429TriphosgeneHCID 178519022HCID 178519022, Verbindung

Produkt 1

HCID 477329[4-(2,6-dichlorophenyl)-1,2,5-thiadiazol-3-yl] N-(2-cyanoethyl)-N-methyl-carbamateAusbeute 290,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 50 mL of dichloromethane, were dissolved 1.98 g of 3-(2,6-dichlorophenyl)-4-hydroxy-1,2,5-thiadiazole, and 0.8 g of bis(trichloromethyl) carbonate. Thereto, 0.7 g of pyridine was added. The mixture was stirred at room temperature for 12 hours. Thereto, 1.51 g of N-(2-cyanoethyl)-N-methylamine was added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into water, and was extracted with dichloromethane. The dichloromethane layer was washed with dilute hydrochloric acid, 10% sodium hydrogencarbonate, and water successively, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography to obtain 2.8 g of N-(2-cyanoethyl)-N-methyl [3-(2,6-dichlorophenyl)-1,2,5-thiadiazo1-4-yl] carbamate.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. extractionwas extracted with dichloromethane
  3. washThe dichloromethane layer was washed with dilute hydrochloric acid, 10% sodium hydrogencarbonate, and water successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d2c2e94960ec4b22add88e8173067367
Quelldatensatz
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05948916

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