Ammonium Hydroxide → HCID 178507490, compound

HRID 1982132Notes

Reaction equation

HRID 1982132 reaction equation
[Cl:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[N:3]=1.[OH-].[NH4+]>O1CCCC1.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][C:4]1[N:3]=[C:2]([Cl:1])[NH:6][N:5]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 178526581HCID 178526581, compound

Product 1

HCID 178507490HCID 178507490, compound

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.27 g of 5-chloro-3-(o-nitrobenzyl)-1,2,4-triazole in 146 ml of tetrahydrofuran is added to 0° with stirring 146 ml of 20% aqueous solution of titanium trichloride. The mixture is stirred at room temperature overnight basified with concentrated ammonium hydroxide and extracted 3 times with methylene chloride. The combined extracts are dried, evaporated and the residue is crystallized from ether to give 3-(o-aminobenzyl)-5-chloro-1,2,4-triazole, m.p. 162°-165°.

Workup

  1. extractionextracted 3 times with methylene chloride
  2. customThe combined extracts are dried
  3. customevaporated
  4. customthe residue is crystallized from ether

Sources & evidence

ORD record
ord-3d9903c83a20447fb9efa34a13afa487
Source dataset
uspto-grants-1986_06
Patent number
US04595535

Reaction notes

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