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

HRID 325693Notes

Reaction equation

HRID 325693 reaction equation
CSC(=N)[N:4]([C:19]#[N:20])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:18])[CH3:17])[CH:10]=1.[CH3:22][NH:23][NH2:24].[CH3:25][N:26](C)C=O>>[CH3:22][N:23]1[C:19]([NH:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:17])[CH3:18])[CH:10]=2)=[N:20][C:25]([NH2:26])=[N:24]1

Participants

4

Reactant 3

HCID 6061MethylhydrazineHCID 6228DimethylformamideHCID 54462898N-Cyano-N-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]carbamimidothioic acid methyl ester

Product 1

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

Procedure

N-Cyano-N-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-carbamimidothioic acid methyl ester (1.5 g) and N-methylhydrazine (1.2 g) in dimethylformamide (15 ml) were heated at 40° for 24 hours. The solvent was removed, and the residue was triturated with ether to yield the title compound as a white solid (1.0 g) m.p. 95°-96.5°.

Workup

  1. customThe solvent was removed
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-7cf01d215f5e4e0ba9a9b32cbb727d42
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Reaction notes

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