Triethylamine → 5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-3H-1,2,4-triazole-3-thione

HRID 1493000Notes

Reaction equation

HRID 1493000 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[CH3:13][C:14]([C:17]1[CH:18]=[C:19]([C:34]([NH:36][NH2:37])=[NH:35])[CH:20]=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:22]=1[O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])([CH3:16])[CH3:15].C(N(CC)CC)C>O1CCCC1>[CH3:32][C:30]([C:21]1[CH:20]=[C:19]([C:34]2[N:36]=[N:37][C:1](=[S:2])[N:35]=2)[CH:18]=[C:17]([C:14]([CH3:13])([CH3:15])[CH3:16])[C:22]=1[O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])([CH3:31])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 178496297HCID 178496297, compound

Product 1

HCID 189498475-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-3H-1,2,4-triazole-3-thione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Thiocarbonyldiimidazole (0.64 g, 0.0036 mole) is added portionwise to a stirred 0° C. solution of 3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzene carboximidic acid hydrazide (1.0 g, 0.0028 mole) and triethylamine (0.43 ml, 0.003 mole) in tetrahydrofuran (5.0 ml). After the addition is complete the mixture is heated to reflux for 1.5 hours. The solution is cooled and concentrated in vacuo. The residue is dissolved in ether (20 ml) and the solution washed with aqueous 2M HCl, saturated aqueous NaHCO3, saturated aqueous NaCl, and dried over MgSO4. Filtration and concentration in vacuo gives 0.94 g (1.1 g theor., 86%) product after recrystallization from ethyl acetate/isopropyl ether, mp 187° C.

Workup

  1. additionAfter the addition
  2. temperatureis heated
  3. temperatureto reflux for 1.5 hours
  4. temperatureThe solution is cooled
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in ether (20 ml)
  7. washthe solution washed with aqueous 2M HCl, saturated aqueous NaHCO3, saturated aqueous NaCl
  8. dry with materialdried over MgSO4
  9. filtrationFiltration and concentration in vacuo
  10. customgives 0.94 g (1.1 g theor., 86%) product
  11. customafter recrystallization from ethyl acetate/isopropyl ether, mp 187° C.

Sources & evidence

ORD record
ord-9b4188bbb46e430ea6e1e7d99a533f5f
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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