Hydrazine hydrate (1:1) → HCID 19900651, compound

HRID 1029521Notes

Reaction equation

HRID 1029521 reaction equation
[C:1](SC1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1)(=[O:18])[S:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([OH:13])=[C:5]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=1.O.[NH2:36][NH2:37]>ClCCl>[NH:36]([C:1](=[O:18])[S:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([OH:13])=[C:5]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=1)[NH2:37]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21687530HCID 21687530, compound

Product 1

HCID 19900651HCID 19900651, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of S,S-bis[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl] carbonodithioate (5.0 g, 9.9 mmol) in dichloromethane (50 mL) is added dropwise to a 0° C. solution of hydrazine monohydrate (1.1 g, 22.0 mmol) in dichloromethane (60 mL). The ice bath is removed and the reaction is stirred vigorously for 48 hours. The reaction mixture is diluted with ethyl acetate and washed four times with water and once with brine. The organic phase is dried over magnesium sulfate and the solvents are evaporated in vacuo. The residue is chromatographed on a 100 g silica column with ethyl acetate/hexane (1/9 then 1/1). The hydrazide is crystallized from isopropyl ether to give 2.72 g (92%) of S-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl] hydrazinecarbothioate, mp 130.0-131.0° C.

Workup

  1. customThe ice bath is removed
  2. additionThe reaction mixture is diluted with ethyl acetate
  3. washwashed four times with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvents are evaporated in vacuo
  6. customThe residue is chromatographed on a 100 g silica column with ethyl acetate/hexane (1/9
  7. customThe hydrazide is crystallized from isopropyl ether

Sources & evidence

ORD record
ord-d7639fdfbb294336a23156239bc96d9c
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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