Triethylamine → 1-Aminocarbonyl-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole

HRID 2084291Notes

Reaction equation

HRID 2084291 reaction equation
ClC([O:4][C:5](Cl)(Cl)Cl)=O.[CH3:9][C:10]1[C:18]2[C:17](=[O:19])[CH2:16][C:15]([CH3:21])([CH3:20])[CH2:14][C:13]=2[NH:12][N:11]=1.C([N:24](CC)CC)C.[OH-].[NH4+]>ClCCl>[NH2:24][C:5]([N:12]1[C:13]2[CH2:14][C:15]([CH3:21])([CH3:20])[CH2:16][C:17](=[O:19])[C:18]=2[C:10]([CH3:9])=[N:11]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 14923Ammonium HydroxideHCID 178434196HCID 178434196, compound

Product 1

HCID 98593121-Aminocarbonyl-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazoleYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of trichloromethyl chloroformate (0.37 ml, 3.03 mmol) in 3 ml of dichloromethane was added dropwise to a solution of 3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazole (0.4 g, 2.25 mmol), prepared as described in example 15, and triethylamine (0.42 ml, 3.03 mmol) maintained under magnetic stirring and inert atmosphere at about −15° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for about 3.5 hours. A solution of 32% amonium hydroxide (10 ml) was then added while cooling at −15° C. The mixture was kept at room temperature for about 12 hours and the two layers were separated; dichloromethane was washed with water and brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel (cyclohexane:ethyl acetate=20:30), to yield the title compound as a colourless solid (0.170 g, 36%): m.p. 173-175° C.

Workup

  1. customprepared
  2. temperaturemaintained
  3. customat about −15° C
  4. stirringstirring
  5. temperaturewhile cooling at −15° C
  6. waitThe mixture was kept at room temperature for about 12 hours
  7. customthe two layers were separated
  8. washdichloromethane was washed with water and brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customThe residue was chromatographed on silica gel (cyclohexane:ethyl acetate=20:30)

Sources & evidence

ORD record
ord-1ffa7e76dcc74c5eb3828ac2ede01357
Source dataset
uspto-grants-2004_04
Patent number
US06716856B1

Reaction notes

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