Hydrazine → HCID 135786549, compound

HRID 466064Notes

Reaction equation

HRID 466064 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11]2[S:12][C:13](S(C)(=O)=O)=[N:14][N:15]=2)[CH:8]=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[OH:24])([CH3:4])[CH3:3].[NH2:25][NH2:26]>C(O)(C)C>[CH3:22][C:20]([C:7]1[CH:8]=[C:9]([C:11]2[S:12][C:13]([NH:25][NH2:26])=[N:14][N:15]=2)[CH:10]=[C:5]([C:2]([CH3:3])([CH3:1])[CH3:4])[C:6]=1[OH:24])([CH3:21])[CH3:23]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 135786529HCID 135786529, compound

Product 1

HCID 135786549HCID 135786549, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2,6-bis(1,1-dimethylethyl)-4-[5-(methylsulfonyl)-1,3,4-thiadiazole-2-yl]-phenol (4.1 g, 0.0111 mole) in isopropyl alcohol (30 ml) is added hydrazine (5.0 g, 0.10 mole). The resulting mixture is heated at reflux for four hours. The mixture is cooled and concentrated in vacuo. The residue is dissolved in 1:1 ethyl acetate/ether and washed with saturated aqueous NaCl and dried over MgSO4. Filtration and concentration in vacuo provides a solid which is recrystallized from ethanol/water to give 2.6 g of 2,6-bis(1,1-dimethylethyl)-4-(5-hydrazino-1,3,4-thiadiazol-2-yl)phenol after drying in vacuo (3.6 g theor., 73%), mp 109°-122° C.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for four hours
  3. temperatureThe mixture is cooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in 1:1 ethyl acetate/ether
  6. washwashed with saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationFiltration and concentration in vacuo
  9. customprovides a solid which
  10. customis recrystallized from ethanol/water

Sources & evidence

ORD record
ord-21b92d45e54c40a981753205896ba99e
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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