Water → Carboxyamidotriazole

HRID 280654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280654
[NH2:1][C:2]1[NH:6][N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8].[H-].[Na+].[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([C:19]2[C:26]([Cl:27])=[CH:25][C:22]([CH2:23]Br)=[CH:21][C:20]=2[Cl:28])=[O:18])=[CH:15][CH:14]=1.O>CN(C)C=O.C(O)(=O)C>[NH2:1][C:2]1[N:6]([CH2:23][C:22]2[CH:21]=[C:20]([Cl:28])[C:19]([C:17](=[O:18])[C:16]3[CH:15]=[CH:14][C:13]([Cl:12])=[CH:30][CH:29]=3)=[C:26]([Cl:27])[CH:25]=2)[N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 136496564-(4-Chlorobenzoyl)-3,5-dichlorobenzyl bromideHCID 178513860HCID 178513860, Verbindung

Produkt 1

HCID 108144CarboxyamidotriazoleAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred ambient temperature solution of 5-amino-1,2,3-triazole-4-carboxamide (630 mg, 4.96 mmol) in dry dimethylformamide (20 ml) was treated in one portion with sodium hydride (230 mg of a 50% suspension in mineral oil, 115 mg NaH, 4.79 mmol). After 15 min. solid 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl bromide was added in one portion. The mixture was stirred 1 hour, poured into water (20 ml), acidified to pH 6 with glacial acetic acid, and filtered. The solid was washed three times with water and dissolved in dichloromethane. The layers were separated and the organic phase was dried over anhydrous magnesium sulfate and evaporated under vacuum. The residue was chromatographed on a column of silica gel (200 g) eluted with 97:3 (v/v) dichloromethane-methanol to provide 351 mg (17%) 5-amino-1-(4-[4-chlorobenzoyl]-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide.

Aufarbeitung

  1. filtrationfiltered
  2. washThe solid was washed three times with water
  3. dissolutiondissolved in dichloromethane
  4. customThe layers were separated
  5. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was chromatographed on a column of silica gel (200 g)
  8. washeluted with 97:3 (v/v) dichloromethane-methanol

Quellen und Nachweise

ORD-Eintrag
ord-ad84160f5aa440c2886ec6b0f5474767
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590201

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