Water → HCID 70114423, compound

HRID 467639Notes

Reaction equation

HRID 467639 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[Cl-].C[Al+]C.C(O[C:12]([C:14]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]([CH2:22][CH2:23][O:24][CH3:25])[N:15]=1)=[O:13])C.O>C1(C)C=CC=CC=1>[CH3:2][N:3]([CH3:4])[C:12]([C:14]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]([CH2:22][CH2:23][O:24][CH3:25])[N:15]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 16686359Dimethylalumanylium chlorideHCID 70116702HCID 70116702, compound

Product 1

HCID 70114423HCID 70114423, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under inert gas atmosphere, dimethylamine hydrochloride (73 mg, 0.89 mmol) was dissolved in toluene (1.0 ml). Dimethylaluminium chloride (990 μl, 0.9M heptane solution) was added and the reaction mixture was stirred for 10 min. at ambient temperature. 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester (70 mg, 0.29 mmol) was added and the reaction mixture was heated to 90° C. overnight. After cooling-down to ambient temperature, a small amount of water was added and the resulting suspension was stirred vigorously for 5 min. All volatiles were removed and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light brown oil (65 mg, 93%).

Workup

  1. temperaturethe reaction mixture was heated to 90° C. overnight
  2. stirringthe resulting suspension was stirred vigorously for 5 min
  3. customAll volatiles were removed
  4. customthe product was obtained
  5. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-5c87256035254ca4bb04495ff6143e1c
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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