Hydrochloric Acid → Pyrithiobac

HRID 1650080Notes

Reaction equation

HRID 1650080 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].N([O-])=O.[Na+].Cl.[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([SH:28])[N:21]=1.[OH-].[Na+]>O>[Cl:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:3]([S:28][C:22]2[N:21]=[C:20]([O:19][CH3:18])[CH:25]=[C:24]([O:26][CH3:27])[N:23]=2)[C:4]=1[C:5]([OH:7])=[O:6]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 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 nitrite 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 2-chloro-6-[(4,6-dimethoxypyrimidin-2-yl)thio]benzoic acid as ocher powder. Melting point: 148°-151° C.

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-bc02c5a851a44b33a0111ba077214ef6
Source dataset
uspto-grants-1990_05
Patent number
US04923501

Reaction notes

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