Triethylamine → N'-(4-Fluoro-3-methyl-benzoyl)-hydrazinecarboxylic acid tert-butyl ester

HRID 239180Notes

Reaction equation

HRID 239180 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[CH3:11].C(N(CC)CC)C.[C:19]([O:23][C:24]([NH:26][NH2:27])=[O:25])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[C:19]([O:23][C:24]([NH:26][NH:27][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH3:11])[CH:4]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 27745894-Fluoro-3-methylbenzoyl chloride

Product 1

HCID 86686514N'-(4-Fluoro-3-methyl-benzoyl)-hydrazinecarboxylic acid tert-butyl esterYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.2 g 4-fluoro-3-methyl-benzoyl chloride was added to 6.1 g triethylamine and 8 g hydrazinecarboxylic acid tert-butyl ester in 150 mL dichlormethane. The reaction was stirred for 1 h at RT and extracted with water. The organic layer was evaporated and the residue was crystallized from diisopropylether to yield 13 g of the desired product. Rt: 1.22 min (method B) (M+H)+: 269

Workup

  1. extractionextracted with water
  2. customThe organic layer was evaporated
  3. customthe residue was crystallized from diisopropylether

Sources & evidence

ORD record
ord-d6ff8d03fa8342e3a93c550e0d21d3d1
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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