Hydrochloric Acid → 2-(1-Methyl-1H-pyrazol-4-yl)benzenesulfonyl chloride

HRID 1193453Notes

Reaction equation

HRID 1193453 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2N)[CH:4]=[N:3]1.N([O-])=O.[Na+].[ClH:18].[S:19](=[O:21])=[O:20]>C(O)(=O)C.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:19]([Cl:18])(=[O:21])=[O:20])[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 13672714HCID 13672714, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 136727152-(1-Methyl-1H-pyrazol-4-yl)benzenesulfonyl chloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

By the procedure of Example 4, 17.3 g of 1-methyl-4-(2-aminophenyl)-1H-pyrazole prepared in Example 18 was diazotized with 7.2 g of sodium nitrite and 36 ml of concentrated HCl in 104 ml of glacial acetic acid. The diazonium salt suspension was added to a suspension containing 4.3 g of cupric chloride dihydrate, 30 ml of sulfur dioxide and 76 ml of acetic acid. After completion of the reaction and addition of water, the suspension was extracted with 1-chlorobutane. The extraction was dried over sodium sulfate and concentrated in vacuo at less than 40° C. to yield 22 g of crude 2-(1-methyl-1H-pyrazol-4-yl)benzenesulfonyl chloride as an oil.

Workup

  1. extractionthe suspension was extracted with 1-chlorobutane
  2. extractionThe extraction
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated in vacuo at less than 40° C.

Sources & evidence

ORD record
ord-2cd7f3083cd74e4ba0c4ff8efe0ee0bd
Source dataset
uspto-grants-1989_03
Patent number
US04810282

Reaction notes

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