1,2-Dichloroethane → tert-Butyl 2-(4-fluorobenzoyl)hydrazine-1-carboxylate

HRID 1046921Notes

Reaction equation

HRID 1046921 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C=O)C.[C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[NH:17][NH2:18].C(Cl)CCl>C(OCC)C.C1COCC1>[C:21]([O:20][C:16]([NH:17][NH:18][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 99734-Fluorobenzoic AcidHCID 70091tert-Butyl carbazate

Product 1

HCID 67279032tert-Butyl 2-(4-fluorobenzoyl)hydrazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluorobenzoic acid (35.7 mmol) in 72 mL of a mixture of DMF and THF (1:1), is added tert-butyl carbazate (37.5 mmol), EDC (39.3 mmol) and N,N-dimethylaminopyridine (0.54 mmol). After 10 minutes the mixture becomes homogeneous and stirring is continued for 3 hours until the reaction is complete by TLC and LC/MS. The reaction mixture is poured into ice. Upon addition of diethylether the organic layer is separated. The organic layer is washed with sodium bisulfite, saturated sodium bicarbonate and saturated sodium chloride solution, dried over magnesium sulfate and concentrated to yield N′-(4-fluoro-benzoyl)-hydrazinecarboxylic acid tert-butyl ester: MS: (ES+) 255 (M+1)+.

Workup

  1. waitis continued for 3 hours until the reaction
  2. additionThe reaction mixture is poured into ice
  3. customis separated
  4. washThe organic layer is washed with sodium bisulfite, saturated sodium bicarbonate and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac2523e226fc441484b99a8acb011207
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

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