Triethylamine → Ethyl[2-(4-isopropylbenzoyl)hydrazino]acetate

HRID 2172164Notes

Reaction equation

HRID 2172164 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[NH:28]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH2:29]>ClCCl.C1COCC1>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][NH:28][NH:29][C:8](=[O:10])[C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:12][CH:11]=1)[CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108204-Isopropylbenzoic AcidHCID 12509Acetic acid, 2-hydrazinyl-, ethyl esterHCID 62365Isobutyl chloroformate

Product 1

HCID 90697033Ethyl[2-(4-isopropylbenzoyl)hydrazino]acetateYield 97%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., to a solution of 4-isopropylbenzoic acid (3.28 g, 20.0 mmol), triethylamine (2.12 g, 2.93 mL, 21.0 mmol) in dichloromethane/THF (15 mL/5 mL), is added isobutylchloroformate (2.87 g, 2.72 mL, 21.0 mmol). The mixture is stirred at 0° C. for 20 min. with warming to room temperature over 2 hr., and then treated with ethyl hydrazinoacetate (2.18 g, 21.0 mmol) and stirred overnight. The mixture is then washed with water, brine and dried over Na2SO4. The crude product obtained after the removal of the solvent is chromatographed (silica gel, 5:1 dichloromethane-ethyl acetate) to provide ethyl[2-(4-isopropylbenzoyl)hydrazino]acetate (4.85 g, 97%). MS (ES+): m/e 251.

Workup

  1. temperaturewith warming to room temperature over 2 hr
  2. stirringstirred overnight
  3. washThe mixture is then washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product obtained
  6. customafter the removal of the solvent
  7. customis chromatographed (silica gel, 5:1 dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-504200d1381f46fb9041ab306a472784
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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