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

HRID 2058733Notes

Reaction equation

HRID 2058733 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, hydrobromide

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 yeild 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-c9f7ce1f3f034f708e149fc50a3a85d7
Source dataset
uspto-grants-1982_03
Patent number
US04318913

Reaction notes

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