Water → 5-Amino-1-(3,4-dichlorobenzyl)-1,2,3-triazole-4-carboxamide

HRID 2414140Notes

Reaction equation

HRID 2414140 reaction equation
[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:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:16]Cl.O>CN(C)C=O.C(O)(=O)C>[NH2:1][C:2]1[N:6]([CH2:16][C:15]2[CH:18]=[CH:19][C:20]([Cl:21])=[C:13]([Cl:12])[CH:14]=2)[N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydride2×HCID 178513860HCID 178513860, compound

Product 1

HCID 140330335-Amino-1-(3,4-dichlorobenzyl)-1,2,3-triazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred, ambient temperature solution of 5-amino-1,2,3-triazole-4-carboxamide (635 mg, 5.00 mmole) in dry dimethylformamide (20 ml) is treated in one portion with sodium hydride (240 mg of a 50% dispersion in mineral oil, 120 mg NaH, 5.0 mmol). After 15 min 3,4-dichlorobenzyl chloride (0.977 g, 5.00 mmol) is added. The mixture is stirred 1 hour, poured into water (20 ml), acidified to pH 6 with glacial acetic acid, and filtered. The solid is washed with water, dried, and chromatographed to provide 5-amino-1-(3,4-dichlorobenzyl)-1,2,3-triazole-4-carboxamide.

Workup

  1. filtrationfiltered
  2. washThe solid is washed with water
  3. customdried
  4. customchromatographed

Sources & evidence

ORD record
ord-40130363c59e405ea6223a7cb1585755
Source dataset
uspto-grants-1988_01
Patent number
US04721791

Reaction notes

Loading…