Hydrazine → HCID 135786549, compound

HRID 1493013Notes

Reaction equation

HRID 1493013 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-90bd3af297db4222bac75c6e828db6ef
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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