Methanol → HCID 178482804, compound

HRID 1960064Notes

Reaction equation

HRID 1960064 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.COC1C=C(OC)C=CC=1C[NH:18][C:19]([C:21]1[C:25]([N:26]([CH3:37])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=2)=[CH:24][NH:23][N:22]=1)=[O:20].CO.[OH-].[Na+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH3:37][N:26]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=1)[C:25]1[C:21]([C:19]([NH2:18])=[O:20])=[N:22][NH:23][CH:24]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 178491173HCID 178491173, compound

Product 1

HCID 178482804HCID 178482804, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4.45 g of para-toluenesulfonic acid monohydrate are added to a solution of 2.49 g of 4-[methyl(3-nitrobenzyl)amino]-1H-pyrazole-3-carboxylic acid 2,4-dimethoxybenzylamide in 30 ml of toluene, and the reaction medium is then heated at the reflux temperature of the toluene for 17 hours. After cooling the reaction medium to room temperature, 15 ml of methanol are added, followed by 700 ml of ethyl acetate and finally 300 ml of distilled water. The pH of this medium is adjusted to a value of 11 by adding 100 ml of aqueous 1N sodium hydroxide solution. This solution is filtered, the solid is extracted twice with 30 ml of ethyl acetate, and the liquid phases are combined and then separated by settling of the phases. The aqueous phase is extracted with twice 200 ml of methylene chloride, the organic phases are combined, washed with 300 ml of saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. 1.41 g of 4-[methyl(3-nitrobenzyl)amino]-1H-pyrazole-3-carboxamide are obtained in the form of a beige-colored solid melting at 166° C. ([M+H]+): 276). RT: 2.61 min (Method A).

Workup

  1. filtrationThis solution is filtered
  2. extractionthe solid is extracted twice with 30 ml of ethyl acetate
  3. customseparated
  4. extractionThe aqueous phase is extracted with twice 200 ml of methylene chloride
  5. washwashed with 300 ml of saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2ba121a5a4734c3da62a62ba1b0400f2
Source dataset
uspto-grants-2013_04
Patent number
US08410286B2

Reaction notes

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