Water → Carboxyamidotriazole

HRID 280654Notes

Reaction equation

HRID 280654 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: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]

Participants

7

Reactant 4

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

Product 1

HCID 108144CarboxyamidotriazoleYield 17%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ad84160f5aa440c2886ec6b0f5474767
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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