Phosphorus tribromide → 1-Methyl-N5-[3-[3-(bromomethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine, hydrobromide

HRID 35065Notes

Reaction equation

HRID 35065 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH2:18]O)[CH:15]=[CH:16][CH:17]=2)=[N:5][C:4]([NH2:20])=[N:3]1.P(Br)(Br)[Br:22]>C(Cl)Cl>[BrH:22].[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][Br:22])[CH:13]=2)=[N:5][C:4]([NH2:20])=[N:3]1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 212976113-[3-[(1-methyl-3-amino-1H-1,2,4-triazol-5-yl)amino]propoxy]benzene methanol

Product 1

HCID 1317126881-Methyl-N5-[3-[3-(bromomethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine, hydrobromideYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[3-[(1-methyl-3-amino-1H-1,2,4-triazol-5-yl)amino]propoxy]benzene methanol (1.9 g) in methylene chloride (25 ml) was treated with phosphorus tribromide (3.27 g) at room temperature for 76 hrs. The resulting oil was purified by column chromatography using ethyl acetate/methanol, 8:1 as eluant to yield the title compound as a white solid (1.7 g). TLC silica ethyl acetate, water, isopropanol 0.88 ammonia (25:8:15:2) Rf 0.72. m.p. 129°-130°.

Workup

  1. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-a2c3c10a217e48069b2c53da02cfa23d
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

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