3-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine → 1-Methyl-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

HRID 35050Notes

Reaction equation

HRID 35050 reaction equation
CS[C:3]([N:7]([CH3:9])[NH2:8])=[N:4][C:5]#[N:6].[NH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:18]=[CH:19][CH:20]=1>>[CH3:9][N:7]1[C:3]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]([CH3:23])[CH3:24])[CH:16]=2)=[N:4][C:5]([NH2:6])=[N:8]1

Participants

3

Reactant 2

HCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamineHCID 86738283N-cyano-1-methylhydrazinecarboximidothioic acid methyl ester

Product 1

HCID 137898531-Methyl-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamineYield 58.3%

Procedure

A mixture of N-cyano-1-methylhydrazinecarboximidothioic acid methyl ester (200 mg) and 3-(3-aminopropoxy)-N,N-dimethylbenzenemethanamine (289 mg) was heated at 40° under a reduced pressure of 20 mm of mercury for 4 hours. The reaction mixture was cooled, triturated with ether and the resulting solid recrystallised from ethyl acetate to give the title compound as colourless crystals (246 mg) m.p. 95°-96.5°.

Workup

  1. temperaturewas heated at 40° under a reduced pressure of 20 mm of mercury for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. customtriturated with ether
  4. customthe resulting solid recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-ec349841c55d4246a24a799d344dbd5b
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

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