Hydrazine hydrate (1:1) → HCID 19362776, compound

HRID 850284Notes

Reaction equation

HRID 850284 reaction equation
[CH:1]([C:4]1[CH:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[CH:19]=[C:18]([CH:25]([CH3:27])[CH3:26])[C:5]=1[CH2:6][N:7]1C(=O)C2=CC=CC=C2C1=O)([CH3:3])[CH3:2].O.NN>CO>[CH:25]([C:18]1[CH:19]=[C:20]([CH:22]([CH3:24])[CH3:23])[CH:21]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[CH2:6][NH2:7])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 19362775HCID 19362775, compound

Product 1

HCID 19362776HCID 19362776, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of N-(2,4,6-triisopropylbenzyl)phthalimide (4.62 g, 13.7 mmol), hydrazine hydrate (0.5 mL), and methanol (150 mL) was heated on the steambath for 3 hours, at which time 0.3 mL more hydrazine hydrate was added. The reaction mixture was allowed to stand overnight at room temperature. Methanol (150 mL) was added and heated on the steambath. The methanol was removed on the rotary evaporator without heating. The reaction mixture was diluted with water (300 mL) and extracted with dichloromethane (1×200 mL and 1×100 mL), the extracts were combined, dried (magnesium sulfate), filtered, and concentrated. The residue was filtered through silica using ethyl acetate as eluant. The product was obtained as an oil, 1.93 g, (65%).

Workup

  1. additionwas added
  2. temperatureheated on the steambath
  3. customThe methanol was removed on the rotary evaporator
  4. temperaturewithout heating
  5. additionThe reaction mixture was diluted with water (300 mL)
  6. extractionextracted with dichloromethane (1×200 mL and 1×100 mL)
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. filtrationThe residue was filtered through silica
  11. customThe product was obtained as an oil, 1.93 g, (65%)

Sources & evidence

ORD record
ord-c544c0b3c2a54affb632d21ff735379a
Source dataset
uspto-grants-2000_01
Patent number
US06017905

Reaction notes

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