Acetic Acid → 1-Acetyl-2-(4-iso-propylphenyl)-hydrazine

HRID 1604631Notes

Reaction equation

HRID 1604631 reaction equation
C(N=C=NCCCN(C)C)C.Cl.[CH:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[CH:18][CH:17]=1)([CH3:15])[CH3:14].[C:24](O)(=[O:26])[CH3:25].O.ON1C2C=CC=CC=2N=N1>ClCCl.C(N(CC)CC)C>[C:24]([NH:23][NH:22][C:19]1[CH:20]=[CH:21][C:16]([CH:13]([CH3:15])[CH3:14])=[CH:17][CH:18]=1)(=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2733248[4-(Propan-2-yl)phenyl]hydrazine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 196037571-Acetyl-2-(4-iso-propylphenyl)-hydrazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-Ethyl-3-(3'-dimethylamino-propyl)carbodiimide (5.87 ml) was added to a mixture of 4-isopropylphenylhydrazine hydrochloride (5.0 g), acetic acid (1.84 ml), triethylamine (3.73 ml) and 1-hydroxybenzotriazole hydrate (40.4 mg) in dichloromethane (50 ml) under ice-cooling and then the mixture was stirred overnight at room temperature. After removal of solvent by evaporation, the resulting residue was partitioned between diluted hydrochloric acid and ethyl acetate. The organic layer was washed successively with aqueous sodium hydrogen carbonate solution, water, and brine, and was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of dichloromethane and methanol. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 1-acetyl-2-(4-iso-propylphenyl)-hydrazine (3.00 g).

Workup

  1. temperaturecooling
  2. customAfter removal of solvent
  3. customby evaporation
  4. customthe resulting residue was partitioned between diluted hydrochloric acid and ethyl acetate
  5. washThe organic layer was washed successively with aqueous sodium hydrogen carbonate solution, water, and brine
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluted with a mixture of dichloromethane and methanol
  9. additionThe fractions containing the objective compound
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd62da1252f84060be42300f23b98bf6
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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