Water → 1-Methyl-N3-[5-hydroxypentyl]-N5-[3-[3-[(dimethylamino) methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

HRID 2058731Notes

Reaction equation

HRID 2058731 reaction equation
[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][N:19]([CH3:21])[CH3:20])[CH:13]=2)=[N:5][C:4]([NH2:22])=[N:3]1.[OH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=O.[BH4-].[Na+].O>C(O)C>[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][N:19]([CH3:21])[CH3:20])[CH:13]=2)=[N:5][C:4]([NH:22][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][OH:23])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 202055-HydroxypentanalHCID 4311764Sodium borohydrideHCID 137898531-Methyl-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

Product 1

HCID 543486491-Methyl-N3-[5-hydroxypentyl]-N5-[3-[3-[(dimethylamino) methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Methyl-N5 -[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine (1.0 g) and 5-hydroxypentanal (1.9 ml) were heated at reflux in ethanol (30 ml) for 5 h. The solution was cooled at 5° and treated with sodium borohydride (0.76 g). The resulting suspension was stirred at room temperature for 16 h, treated with water and reduced in volume in vacuo. The aqueous solution was extracted with ethyl acetate, and the organic extracts were distilled to give the title compound as a pale yellow oil (0.47 g) b.p. 250°/0.5 mm. TLC silica; ethyl acetate:isopropanol:water: 0.88 ammonia 25:15:8:2, Rf 0.6.

Workup

  1. temperatureThe solution was cooled at 5°
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. distillationthe organic extracts were distilled

Sources & evidence

ORD record
ord-cb7752d425f14d82958ce3923fd45f6f
Source dataset
uspto-grants-1982_03
Patent number
US04318913

Reaction notes

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