Hydrochloric Acid → Pyrithiobac

HRID 2106966Notes

Reaction equation

HRID 2106966 reaction equation
Cl.N[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:4]=1[C:5]([OH:7])=[O:6].Cl.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[N:19]=[C:18]([SH:24])[N:17]=1.[OH-].[Na+]>O>[Cl:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:3]([S:24][C:18]2[N:17]=[C:16]([O:15][CH3:14])[CH:21]=[C:20]([O:22][CH3:23])[N:19]=2)[C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 53444447HCID 53444447, compoundHCID 178493561HCID 178493561, compound

Product 1

HCID 91781PyrithiobacYield 22.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g of 2-amino-6-chlorobenzoic acid hydrochloride was converted to a diazonium salt with 2.3 g of sodium nitride and concentrated hydrochloric acid. Then, this diazonium salt was gradually dropwise added to a solution comprising 4.8 g of 4,6-dimethoxy-2-mercaptopyrimidine, 2.4 g of sodium hydroxide and 40 ml of water at 0° C. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours to complete the reaction. Concentrated hydrochloric acid was added to the reaction solution, and then, the mixture was extracted with ethyl acetate. The extract was dried, and then the solvent was distilled off under reduced pressure. The residue thereby obtained was purified by column chromatography to obtain 1.8 g of the desired compound as ocher powder.

Workup

  1. customat 0° C
  2. additionAfter completion of the dropwise addition
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe extract was dried
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue thereby obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ad6f34de46ba4188a8fdee6e9555420b
Source dataset
uspto-grants-1990_06
Patent number
US04932999

Reaction notes

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