Sulfuric Acid → HCID 178503611, compound

HRID 2407166Notes

Reaction equation

HRID 2407166 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[C:10]([OH:12])=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(=O)(=O)(O)O.[NH:19]([C:21]([S:23][CH3:24])=[NH:22])[NH2:20]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:20]=[N:19][C:21]([S:23][CH3:24])=[N:22][C:10]=2[OH:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 20608072HCID 20608072, compoundHCID 178504051Methyl hydrazinecarbimidothioate

Product 1

HCID 178503611HCID 178503611, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

(3,5-Dichlorophenyl)(oxo)acetic acid (28.0 g 129.0 mmol) was dissolved in ethanol (280 mL) and treated successively with a catalytic quantity of sulfuric acid and methyl hydrazinecarbimidothioate (20.5 g, 193.5 mmol). The resulting mixture was stirred for 1 hr at 78° C. After completion of the reaction (TLC), the mixture was concentrated in vacuo, poured into water (150 mL), and extracted with DCM (3×250 ml). The combined organic extracts were then dried over Na2SO4, concentrated in vacuo, and purified by gradient flash chromatography, affording 6-(3,5-dichlorophenyl)-3-(methylthio)-1,2,4-triazin-5-ol (19 g, 46%).

Workup

  1. customAfter completion of the reaction (TLC)
  2. concentrationthe mixture was concentrated in vacuo
  3. additionpoured into water (150 mL)
  4. extractionextracted with DCM (3×250 ml)
  5. dry with materialThe combined organic extracts were then dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by gradient flash chromatography

Sources & evidence

ORD record
ord-26e556d14f7143bb88885f89d88e3ca9
Source dataset
uspto-grants-2014_08
Patent number
US08809525B2

Reaction notes

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