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

HRID 336368Notes

Reaction equation

HRID 336368 reaction equation
[Br: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]([Br: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 70215344-Bromo-3-methylbenzoyl chloride

Product 1

HCID 86690170N'-(4-bromo-3-methyl-benzoyl)-hydrazinecarboxylic acid tert-butyl esterYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

54.3 g 4-bromo-3-methyl-benzoyl chloride was added to 23.3 g triethylamine and 30.4 g hydrazinecarboxylic acid tert-butyl ester in 1 L dichlormethane. The reaction was stirred 1 h at RT and extracted with water. The organic layer was evaporated and the residue was crystallized with diisopropylether to give 70 g desired product.

Workup

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

Sources & evidence

ORD record
ord-eb0aaaf6f5234b76866f8d8fb0c4cd9b
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

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