Sodium Iodide → 1-Methyl-3-(1-pyrrolidinyl)-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-5-amine

HRID 35059Notes

Reaction equation

HRID 35059 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](Cl)=[N:3]1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[I-].[Na+]>Cl>[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]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[N:3]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 31268PyrrolidineHCID 54556689HCID 54556689, compound

Product 1

HCID 539754321-Methyl-3-(1-pyrrolidinyl)-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-5-amineYield 61%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1-methyl-3-chloro-N5 -[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-5-amine (0.4 g), pyrrolidine (0.71 g) and sodium iodide (0.3 g) was heated at 180° in an autoclave for 16 hr. The reaction mixture was dissolved in dilute hydrochloric acid, washed with ethyl acetate, basified with sodium hydroxide and extracted with toluene. The toluene extracts were fractionally distilled to give the title compound as a pale yellow oil (0.27 g) b.p. 210° (0.04 mm). TLC silica; ethyl acetate:isopropanol:water:0.88 ammonia 25:15:8:2; Rf 0.6.

Workup

  1. temperaturewas heated at 180° in an autoclave for 16 hr
  2. washwashed with ethyl acetate
  3. extractionextracted with toluene
  4. distillationThe toluene extracts were fractionally distilled

Sources & evidence

ORD record
ord-c4aab881ba304b8ea0dd6829386c2198
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

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