Chlorosulfonic acid → HCID 58152678, compound

HRID 471333Notes

Reaction equation

HRID 471333 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][CH:7]([F:21])[C:8]1[N:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[CH3:20])[N:9]=1>C(Cl)Cl>[F:21][CH:7]([F:6])[C:8]1[N:12]=[CH:11][N:10]([C:13]2[C:14]([CH3:20])=[CH:15][C:16]([CH3:19])=[C:17]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:18]=2)[N:9]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 50991268HCID 50991268, compound

Product 1

HCID 58152678HCID 58152678, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

Under a nitrogen atmosphere, 14.2 g of chlorosulphonic acid are introduced and are admixed at room temperature, in portions, with 4 g of 3-(difluoromethyl)-1-(2,4-dimethylphenyl)-1H-1,2,4-triazole. The exothermic reaction raises the temperature of the mixture to around 45° C. The mixture is subsequently stirred at 70° C. for 5 hours and then cooled, and diluted with 20 ml of methylene chloride. The mixture is added with stirring to 40 g of ice and then the phases are separated and extracted with twice 20 ml of methylene chloride. The combined organic phases are concentrated on a rotary evaporator. This gives 4.5 g of brown oil. This oil is chromatographed using CH2Cl2. A white solid (2.9 g; 52% of theory) is isolated.

Workup

  1. customThe exothermic reaction
  2. temperaturecooled
  3. additionThe mixture is added
  4. customthe phases are separated
  5. extractionextracted with twice 20 ml of methylene chloride
  6. concentrationThe combined organic phases are concentrated on a rotary evaporator
  7. customThis oil is chromatographed
  8. customA white solid (2.9 g; 52% of theory) is isolated

Sources & evidence

ORD record
ord-80b0812e64fb49f4a68f3ec1f5435909
Source dataset
uspto-grants-2014_01
Patent number
US08632767B2

Reaction notes

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