Triethylamine → HCID 136352997, compound

HRID 336839Notes

Reaction equation

HRID 336839 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.Cl.[CH3:17][NH:18][O:19][CH3:20].C(N(CC)CC)C>ClCCCl.O.CN(C)C=O>[CH3:20][O:19][N:18]([CH3:17])[C:9]([C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[NH:8][N:7]=1)=[O:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 862226845-Nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 136352997HCID 136352997, compoundYield 91.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 20.4 g (130.31 mmol) of 5-nitro-1H-pyrazole-3-carboxylic acid in suspension in 530 ml of 1,2-dichloroethane, are respectively added 28.36 ml (390.93 mmol) of thionyl chloride and 4 ml of dimethylformamide. The suspension is stirred under reflux for 8 h. The reaction mixture is then cooled to room temperature and the precipitate is filtered. The precipitate is re-suspended in 330 ml of dichloromethane after which are successively added 15.25 g (156.37 mmol) of N,O-dimethylhydroxylamine hydrochloride and 39.56 g (390.93 mmol) of triethylamine. The reaction mixture is stirred for 18 h at room temperature, water is added and the product is extracted several times with dichloromethane then with a dichloromethane/methanol mixture (90:10). The organic phases are combined, dried over magnesium sulfate and concentrated to yield 23.88 g of N-methoxy-N-methyl-5-nitro-1H-pyrazol-3-carboxamide in the form of a white solid.

Workup

  1. temperatureunder reflux for 8 h
  2. filtrationthe precipitate is filtered
  3. stirringThe reaction mixture is stirred for 18 h at room temperature
  4. extractionthe product is extracted several times with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c0f24c4d041043429e818a0946ce983c
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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