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

HRID 325711Notes

Reaction equation

HRID 325711 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-3e969f534cb74a2fa9bb8b8b3a8396ca
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Reaction notes

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