tert-Butyl carbazate → 5-Methyl-2-furohydrazide

HRID 1259872

Reaction equation

HRID 1259872 reaction equation
C(OC(C)(C)C)(=O)[NH:2][NH2:3].[CH3:10][C:11]1[O:15][C:14]([C:16](Cl)=[O:17])=[CH:13][CH:12]=1>C(Cl)Cl>[CH3:10][C:11]1[O:15][C:14]([C:16]([NH:2][NH2:3])=[O:17])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 27598515-Methylfuran-2-carbonyl chloride

Product 1

HCID 41592505-Methyl-2-furohydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl carbazate (549 mg, 4.15 mmol) was added to a methylene chloride (10 mL) solution of commercially available 5-methylfuran-2-carbonyl chloride (500 mg, 3.46 mmol) under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated, and then, the residue was dissolved in methylene chloride (10 mL). To the solution, trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was concentrated to obtain 5-methylfuran-2-carbohydrazide.

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue was dissolved in methylene chloride (10 mL)
  3. additionTo the solution, trifluoroacetic acid (2 mL) was added
  4. stirringthe mixture was stirred at room temperature for 1.5 hours
  5. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-694b64273cac4806be76eab314deb09a
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Linked notes

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