Benzenesulfonyl chloride → HCID 20335988, compound

HRID 1706394Notes

Reaction equation

HRID 1706394 reaction equation
[NH2-:1].[Na+].[CH3:3][N:4]1[CH2:8][CH:7](O)[CH2:6][N:5]1[CH3:10].[C:11]1(S(Cl)(=O)=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH:1]([CH:7]1[CH2:8][N:4]([CH3:3])[N:5]([CH3:10])[CH2:6]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 24533Sodium amideHCID 12543340HCID 12543340, compound

Product 1

HCID 20335988HCID 20335988, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred suspension of 40 g. (1.02 mole) of sodamide in dry toluene was treated dropwise with 116 g. (1.0 mole) of 1,2-dimethyl-4-pyrazolidinol at 80° C. After 4.5 hrs. at reflux the mixture was cooled and maintained below 20° C. while 161.0 g. (1.0 mole) of benzenesulfonyl chloride was added dropwise. After stirring 1.0 hr. the reaction mixture was shaken with dilute sodium hydroxide, the separated toluene layer dried over sodium sulfate and concentrated at reduced pressure. The residue was dissolved in 300 ml. of aniline, the mixture heated 2.5 hrs. on the steam bath and refluxed for 3.0 hrs. The cooled mixture was extracted with dilute sodium hydroxide solution and the separated aqueous layer extracted with isopropyl ether. The combined organic layers after drying over sodium sulfate were concentrated and the residue distilled to a pot temperature of 140° C./80 mm. The residue which would not crystallize was distilled at 110°-125° C./0.1 mm. to give 86 g. of product.

Workup

  1. additionA stirred suspension of 40 g
  2. customat 80° C
  3. temperatureat reflux the mixture
  4. temperaturewas cooled
  5. temperaturemaintained below 20° C. while 161.0 g
  6. dry with materialthe separated toluene layer dried over sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. dissolutionThe residue was dissolved in 300 ml
  9. temperatureof aniline, the mixture heated 2.5 hrs
  10. temperatureon the steam bath and refluxed for 3.0 hrs
  11. extractionThe cooled mixture was extracted with dilute sodium hydroxide solution
  12. extractionthe separated aqueous layer extracted with isopropyl ether
  13. dry with materialThe combined organic layers after drying over sodium sulfate
  14. concentrationwere concentrated
  15. distillationthe residue distilled to a pot temperature of 140° C./80 mm
  16. customThe residue which would not crystallize
  17. distillationwas distilled at 110°-125° C./0.1 mm
  18. customto give 86 g

Sources & evidence

ORD record
ord-e7843289843f43398705ba2c6a6b1723
Source dataset
uspto-grants-1980_06
Patent number
US04207327

Reaction notes

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