Triethylamine → 1-(4-Chlorophenyl)cyclopropanecarbohydrazide

HRID 1423970Notes

Reaction equation

HRID 1423970 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(OC(C)(C)C)(=O)[NH:15][NH2:16].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([NH:15][NH2:16])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 227221341-(4-Chlorophenyl)cyclopropanecarbohydrazideYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-chlorophenyl)-1-cyclopropanecarboxylic acid (9.83 g, 50 mmol), tert-butyl carbazate (7.93 g, 60 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (10.54 g, 55 mmol), 1-hydroxybenzotriazole monohydrate (7.43 g, 55 mmol), and triethylamine (12.65 mL, 125 mmol) in N,N-dimethylformamide (100 mL) was stirred overnight at room temperature. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution and then dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. A 4 M solution (62.5 mL) of hydrochloric acid in 1,4-dioxane and methanol (200 mL) were added to the partially purified product, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, dichloromethane was added to the residue, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution and then dried with anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, hexane was added to the obtained partially purified product, and the solid was collected by filtration to obtain the title compound (9.06 g, 86%) as a light brown solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionA 4 M solution (62.5 mL) of hydrochloric acid in 1,4-dioxane and methanol (200 mL) were added to the partially purified product
  7. concentrationThe reaction mixture was concentrated under reduced pressure, dichloromethane
  8. additionwas added to the residue
  9. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution
  10. dry with materialdried with anhydrous sodium sulfate
  11. concentrationThe filtrate was concentrated under reduced pressure, hexane
  12. additionwas added to the
  13. customobtained partially purified product
  14. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-1d896e22d50343199ce442d3ecfaff85
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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