2-Methyl-2-thiopseudourea sulfate → HCID 13088591, compound

HRID 2164700Notes

Reaction equation

HRID 2164700 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.S(O)(O)(=O)=O.[CH3:26][S:27]C(=N)N.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([S:27][CH3:26])[CH:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 516892Sodium BicarbonateHCID 540228171-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one

Product 1

HCID 13088591HCID 13088591, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

289 g (1 mol) of 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one (E,Z isomer mixture) and 139 g (0.5 mol) of S-methylisothiourea sulphate were suspended in 2.5 liters of ethanol and 336 g (4 mol) of sodium bicarbonate were added in portions, while stirring. The mixture was heated under reflux for 4 hours, cooled to room temperature and poured onto water. The organic constituents were extracted with methylene chloride. The organic phase was dried over sodium sulphate, filtered and evaporated down. The resulting oil was caused to crystallize by stirring it with diisopropyl ether, and the crystals were recrystallized from ethanol. 42 g (12% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-1-methylthio-2-(1,2,4-triazol-1-yl)-pentan-3-one of melting point 145° C. were obtained. ##STR13## Process variant (c):

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. additionpoured onto water
  4. extractionThe organic constituents were extracted with methylene chloride
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated down
  8. customto crystallize
  9. stirringby stirring it with diisopropyl ether
  10. customthe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-c064a24af5a944ee918388c0b3920c99
Source dataset
uspto-grants-1985_03
Patent number
US04507141

Reaction notes

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