Hydrazine hydrate (1:1) → 5-tert-Butyl-2-[(2-ethylhexyl)sulfanyl]aniline

HRID 1180718Notes

Reaction equation

HRID 1180718 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:14][CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[C:9]([N+:11]([O-])=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>CC(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:14][CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[C:9]([CH:10]=1)[NH2:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 100419015-tert-butyl-2-(2-ethylhexylthio)nitrobenzene

Product 1

HCID 103570715-tert-Butyl-2-[(2-ethylhexyl)sulfanyl]aniline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a typical example of a specific production method, ferric chloride hexahydrate and an activated carbon are added to a 2-propanol solution of 5-tert-butyl-2-(2-ethylhexylthio)nitrobenzene, and the mixture is refluxed under heating for 10 minutes. To this solution is added, dropwise, an aqueous 80% solution of hydrazine monohydrate. After the addition is finished, the reaction is continued under refluxing until the raw material disappears. Then, the reaction solution is cooled, and the catalyst and the activated carbon are separated by filtration. Toluene is added to the filtrate, and the toluene solution is then washed with water, washed with an acid, neutralized, washed with water, and then concentrated, to obtain 5-tert-butyl-2-(2-ethylhexylthio)aniline.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for 10 minutes
  3. additionTo this solution is added
  4. additionAfter the addition
  5. temperatureThen, the reaction solution is cooled
  6. customthe catalyst and the activated carbon are separated by filtration
  7. additionToluene is added to the filtrate
  8. washthe toluene solution is then washed with water
  9. washwashed with an acid
  10. washwashed with water
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0d9230cca3a3458686ca2c824b0c2eed
Source dataset
uspto-grants-2007_10
Patent number
US07282610B2

Reaction notes

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