Formaldehyde → HCID 178491173, compound

HRID 1668340Notes

Reaction equation

HRID 1668340 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[C:13]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[CH:12][NH:11][N:10]=1)=[O:8].C=O.S([O-])([O-])(=O)=O.[Mg+2].[C:39]([BH3-])#N.[Na+].[OH-].[Na+].[Cl-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[C:13]([N:14]([CH3:39])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[CH:12][NH:11][N:10]=1)=[O:8]

Participants

8

Reactant 6

HCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 178491172HCID 178491172, compound

Product 1

HCID 178491173HCID 178491173, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.61 g of 4-(3-nitrobenzylamino)-1H-pyrazole-3-carboxylic acid 2,4-dimethoxybenzylamide, 1.25 g of paraformaldehyde and 0.94 g of anhydrous magnesium sulfate in 70 ml of glacial acetic acid is stirred at room temperature for 4 hours. 1.23 g of sodium cyanoborohydride are then added portionwise to this solution. The reaction medium is stirred for 2 hours at room temperature, and then poured onto 300 ml of aqueous 5N sodium hydroxide solution and 120 g of crushed ice, the pH being adjusted to 11. 300 ml of saturated sodium chloride solution are then added. This solution is filtered and the solid is washed three times with 60 ml of distilled water. The solid thus collected is air-dried. 1.51 g of 4-[methyl(3-nitrobenzyl)amino]-1H-pyrazole-3-carboxylic acid 2,4-dimethoxybenzylamide are obtained in the form of a pale yellow solid. ([M+H]+): 426). RT: 3.87 min (Method A).

Workup

  1. filtrationThis solution is filtered
  2. washthe solid is washed three times with 60 ml of distilled water
  3. customThe solid thus collected
  4. customis air-dried

Sources & evidence

ORD record
ord-aa88ad2276e0445da4e3ae6755fe032e
Source dataset
uspto-grants-2011_08
Patent number
US07989439B2

Reaction notes

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