Hydrochloric Acid → 1-Methyl-N5-[3-[3-(1-pyrrolidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

HRID 2058718Notes

Reaction equation

HRID 2058718 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[O:10][CH2:11][CH2:12][CH2:13][NH2:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.CS[C:20]([N:24]([CH3:33])[N:25]=CC1C=CC=CC=1)=[N:21][C:22]#[N:23].Cl>CC(C)=O>[CH3:33][N:24]1[C:20]([NH:14][CH2:13][CH2:12][CH2:11][O:10][C:9]2[CH:15]=[CH:16][CH:17]=[C:7]([CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)=[N:21][C:22]([NH2:23])=[N:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 127974543-{3-[(Pyrrolidin-1-yl)methyl]phenoxy}propan-1-amineHCID 54323404methyl N-cyano-1-methyl-2-(phenylmethylene)-hydrazinecarboximidothioate

Product 1

HCID 541994111-Methyl-N5-[3-[3-(1-pyrrolidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamineYield 14.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-[3-[1-pyrrolidinylmethyl]phenoxy]propanamine (0.97 g) and N-cyano-1-methyl-2-(phenylmethylene)hydrazine carboximidothioic acid methyl ester (0.97 g) was heated at 70° for 8 hr under a reduced pressure of 20 mm of mercury. Acetone was added and the solution was treated with hydrochloric acid at room temperature for one hour, washed with ether, basified with sodium carbonate and extracted with ethyl acetate. Evaporation of the ethyl acetate extracts gave a thick oil which crystallised from ethyl acetate/light petroleum (b.p. 60°-80° ) to give the title compound as a white solid (0.2 g). TLC; silica/methanol/0.88 ammonia 80:1) Rf 0.5, m.p. 95°-95.5°.

Workup

  1. temperaturewas heated at 70° for 8 hr under a reduced pressure of 20 mm of mercury
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. customEvaporation of the ethyl acetate
  5. customextracts gave a thick oil which
  6. customcrystallised from ethyl acetate/light petroleum (b.p. 60°-80° )

Sources & evidence

ORD record
ord-8e8b54ee863a4febafb211feff2c5350
Source dataset
uspto-grants-1982_03
Patent number
US04318913

Reaction notes

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