Sodium Bicarbonate → HCID 15837890, compound

HRID 1081883Notes

Reaction equation

HRID 1081883 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([NH:16][CH3:17])[CH:10]=2)=[C:4]([CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH:3]=1.[N:24]([O-])=O.[Na+].C(=O)([O-])O.[Na+]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:15]=[CH:14][C:12]3[N:13]=[N:24][N:16]([CH3:17])[C:11]=3[CH:10]=2)=[C:4]([CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23363126HCID 23363126, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 15837890HCID 15837890, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The aniline derivative was dissolved in 10% H2SO4 (2 ml) under ice cooling, followed by addition of an aqueous solution (0.5 ml) of sodium nitrite (50 mg), and the temperature of the resulting solution was raised up to room temperature for subsequent stirring for 20 hours. The solution was neutralized with an aqueous sodium hydrogen carbonate solution, and the mixture was 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 purified by chromatography on a silica gel column (methylene chloride:methanol=99:1 to 98:2), to give the title compound (55 mg; 41%). The purity of the compound was 100 % by HPLC.

Workup

  1. extractionthe mixture was extracted 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. customThe resulting residue was purified by chromatography on a silica gel column (methylene chloride:methanol=99:1 to 98:2)

Sources & evidence

ORD record
ord-c8f4f93e44c042feaa67ba94e074bb2e
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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