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

HRID 1194721Notes

Reaction equation

HRID 1194721 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 140330315-Amino-1-(4-cyano-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamideYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-21702f4c6a934a54bc6e4f70b1cf0177
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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