tert-Butyl carbazate → Tert-butyl 2-[(4-bromophenyl)acetyl]hydrazinecarboxylate

HRID 1465429Notes

Reaction equation

HRID 1465429 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[NH:13][NH2:14].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:14][NH:13][C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 70091tert-Butyl carbazateHCID 74654Benzeneacetic acid, 4-bromo-HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 67029623Tert-butyl 2-[(4-bromophenyl)acetyl]hydrazinecarboxylateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Bromophenyl)acetic acid (20 g, 93 mmol), tert-butyl carbazate (14.7 g, 111 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21.4 g, 112 mmol) and 1-hydroxybenzotriazole monohydrate (17.1 g, 112 mmol) were dissolved in dichloromethane (400 ml), and N,N-diisopropylethylamine (80 ml) was added. After stirring at room temperature for 16 hrs, the reaction mixture was washed with 1M hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentration residue was purified by silica gel column chromatography (dichloromethane:methanol=99:1→90:10) to give tert-butyl 2-[(4-bromophenyl)acetyl]hydrazinecarboxylate (27 g, yield 88%) as a white solid.

Workup

  1. washthe reaction mixture was washed with 1M hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe concentration residue was purified by silica gel column chromatography (dichloromethane:methanol=99:1→90:10)

Sources & evidence

ORD record
ord-2db68f29434b41a68eb070d50b3bebca
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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