Sulfuryl chloride → HCID 54374869, compound

HRID 1078612Notes

Reaction equation

HRID 1078612 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[S:11])[CH:3]=1.S(Cl)(Cl)(=O)=O>C(Cl)(Cl)Cl>[CH3:8][C:6]1[N:5]2[S:11][C:10](=[N:12][S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:14])=[O:15])[N:9]=[C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 19428231HCID 19428231, compound

Product 1

HCID 54374869HCID 54374869, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 1-(4,6-dimethyl-2-pyridyl)-3-(4-methylphenyl)sulfonyl-2-thiourea (2.90 g) and chloroform (50 ml), sulfuryl chloride (1.28 g) was added. After being stirred at room temperature for 15 minutes, the mixture was refiuxed with heating for 30 minutes. The reaction mixture was concentrated, and the resulting crystal was collected by filtration and suspended in water. After pH adjustment to 7 by the addition of saturated aqueous sodium bicarbonate, the suspension was stirred at room temperature for 1 hour. The separating crystal was collected by filtration and recrystallized from chloroform-methanol to yield 5, 7-dimethyl-2-(4-methylphenyl) sulfonylimino-2H-[1,2,4]thiadiazolo[2,3- a]pyridine (2.40 g, yield 83%) as a colorless needle.

Workup

  1. additionwas added
  2. temperaturewith heating for 30 minutes
  3. concentrationThe reaction mixture was concentrated
  4. filtrationthe resulting crystal was collected by filtration
  5. additionAfter pH adjustment to 7 by the addition of saturated aqueous sodium bicarbonate
  6. stirringthe suspension was stirred at room temperature for 1 hour
  7. filtrationThe separating crystal was collected by filtration
  8. customrecrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-1c32187391094ba599a1e807417752ad
Source dataset
uspto-grants-1996_08
Patent number
US05550138

Reaction notes

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