Sodium Bicarbonate → HCID 178478215, compound

HRID 1081872Notes

Reaction equation

HRID 1081872 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([NH2:14])[CH:8]=2)=[C:4]([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH:3]=1.[N:23]([O-])=O.[Na+].C(=O)([O-])O.[Na+]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]3[NH:13][N:23]=[N:14][C:9]=3[CH:8]=2)=[C:4]([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23363131HCID 23363131, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178478215HCID 178478215, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-[4-Chloro-2-(1H-1,2,4-triazol-1-ylmethyl)phenoxy]-1,2-phenylenediamine (3.2 g) from Example 39 was dissolved with 10% H2SO4 (30 ml) under ice cooling, followed by addition of an aqueous solution (3 ml) of sodium nitrite (1.4 g), and the temperature of the resulting solution was raised up to room temperature for stirring for 2 hours. The solution was neutralized, with an aqueous sodium hydrogen carbonate, and then extracted twice with methylene chloride. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was washed with ether, to give the title compound (3 g; 91%). The purity of the compound was 99.1% by HPLC.

Workup

  1. extractionextracted twice with methylene chloride
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. washThe resulting residue was washed with ether

Sources & evidence

ORD record
ord-65cc77087f534fc09189d821ddc8b75d
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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