Triethylamine → HCID 57941390, compound

HRID 1438049Notes

Reaction equation

HRID 1438049 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:10])[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1B(O)O.C(N(CC)CC)C>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]([CH3:10])[NH:9][C:16]1[CH:17]=[C:12]([Cl:11])[CH:13]=[CH:14][C:15]=1[Cl:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27733712,5-Dichlorobenzeneboronic acidHCID 37482801-Boc-1-methylhydrazine2×

Product 1

HCID 57941390HCID 57941390, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 650 mg, 4.45 mmol), 2,5-dichlorophenylboronic acid (Aldrich; 831 mg, 4.36 mmol), copper(II) acetate (807 mg, 4.45 mmol) and triethylamine (623 μL, 4.45 mmol) in 1,2-dichloroethane (4.5 mL) was heated in an oil bath at 50° C. for 3 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 40 g column, eluting with 20-40% ethyl acetate/hexanes, to give N′-(2,5-dichloro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (592 mg, 46%) as a yellow oil that solidified on standing.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 20-40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2156eabb7fb8474aab56fe51772a9bfd
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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