HCID 20199116, compound → HCID 178484942, compound

HRID 652103Notes

Reaction equation

HRID 652103 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]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:13]=2)=[N:5][C:4]([CH2:25][NH2:26])=[N:3]1>C(OCC)C>[C:4]([NH:5][C:6]([NH:2][CH3:1])=[N:26][CH2:25][C:4]1[N:5]=[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]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:13]=2)[N:2]([CH3:1])[N:3]=1)#[N:3]

Participants

3

Reactant 1

HCID 20199116HCID 20199116, compound

Product 1

HCID 178484942HCID 178484942, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-methanamine (1.0 g) in diethylether (20 ml) was added to a refluxing solution of N-cyanocarbimidothioic acid dimethyl ester (0.45 g) in ether (50 ml) and the mixture heated at reflux for 8 h. After cooling, a colourless solid (0.65 g) precipitated and was collected by filtration, m.p. 121°-122°. This material was added to a solution of methylamine (33% in ethanol, 10 ml) in ethanol (50 ml) and the solution heated at reflux for 16 h. The mixture was evaporated to give a solid which was recrystallized from ethyl acetate to give the title compound as a colourless solid (0.34 g), m.p. 138°-139°.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 8 h
  3. temperatureAfter cooling
  4. customa colourless solid (0.65 g) precipitated
  5. filtrationwas collected by filtration, m.p. 121°-122°
  6. additionThis material was added to a solution of methylamine (33% in ethanol, 10 ml) in ethanol (50 ml)
  7. temperaturethe solution heated
  8. temperatureat reflux for 16 h
  9. customThe mixture was evaporated
  10. customto give a solid which
  11. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cdd1c736165f4250a4e634e09d9fcc31
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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