Sodium hydride → 5-Amino-1-(4-cyano-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide

HRID 1194721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1194721
[NH2:1][C:2]1[NH:6][N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8].[H-].[Na+].[C:12]([C:14]1[C:21]([Cl:22])=[CH:20][C:17]([CH2:18]Cl)=[CH:16][C:15]=1[Cl:23])#[N:13]>CN(C)C=O>[NH2:1][C:2]1[N:6]([CH2:18][C:17]2[CH:16]=[C:15]([Cl:23])[C:14]([C:12]#[N:13])=[C:21]([Cl:22])[CH:20]=2)[N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8]

Komponenten

5

Edukt 3

HCID 24758Sodium hydride2×HCID 230362434-Cyano-3,5-dichlorobenzyl chlorideHCID 178513860HCID 178513860, Verbindung

Produkt 1

HCID 140330315-Amino-1-(4-cyano-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamideAusbeute 23,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred, ambient temperature solution of 5-amino-1,2,3-triazole-4-carboxamide (630 mg, 5.0 mmol) in dry N,N-dimethylformamide (20 ml) was treated with sodium hydride (250 mg of a 50% dispersion in mineral oil, 125 mg NaH, 5.2 mmol). The resulting suspension was stirred 10 min., 4-cyano-3,5-dichlorobenzyl chloride (1.1 g, 5.0 mmol) was added, and the mixture was stirred 2 hours. The reaction was quenched by pouring into ice and water (80 ml). The suspension was filtered and washed three times with water. The solid was suspended in 19:1 (v/v) dichloromethane-methanol and filtered to provide 364 mg (23%) 5-amino-1-(4-cyano-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide. Recrystallization from ethanol provided material of m.p 238°-239.5° C.

Aufarbeitung

  1. stirringthe mixture was stirred 2 hours
  2. customThe reaction was quenched
  3. additionby pouring into ice and water (80 ml)
  4. filtrationThe suspension was filtered
  5. washwashed three times with water
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-21702f4c6a934a54bc6e4f70b1cf0177
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04816469

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