Sulfuric Acid → HCID 67249477, compound

HRID 1964169Notes

Reaction equation

HRID 1964169 reaction equation
[CH:1]1([C:6]2[CH:13]=CC=[CH:10][C:7]=2[C:8]#[N:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)=O.[CH3:17][CH:18](O)[CH3:19].S(=O)(=O)(O)O.O1COCOC1.[Cl:32]S(O)(=O)=O>>[Cl:32][CH2:17][C:18]1[CH:19]=[CH:13][C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 80811,3,5-TrioxaneHCID 24638Chlorosulfonic acidHCID 10487385HCID 10487385, compoundHCID 86586944Isopropanol carbon dioxide

Product 1

HCID 67249477HCID 67249477, compound

Conditions

Temperature
-7 °C

Procedure

2-Cyclopentylbenzonitrile (1.3 g, 7.59 mmol) was transferred into a 2-necked RB flask, fitted with an addition funnel and dry nitrogen inlet. The starting material was stirred and cooled to −22° C. (dry ice/IPA bath). Sulfuric acid (3.25 mL, 61.0 mmol) was added in drops. 1,3,5-Trioxane (0.877 mL, 11.39 mmol) was added in 3 batches (The batches were added fairly quickly, one after another). Almost immediately, chlorosulfonic acid (0.915 mL, 13.67 mmol) was added in drops. Then the reaction mixture (dark brown in color) was allowed to warm up to −7° C. (over approx 15 min). It was stirred at between 6.9° C. and −5° C. for 1.5 h. The reaction was quenched by slowly pouring into ice water. MTBE was added and the mixture was stirred well and filtered through Celite®. The Celite® bed was washed with MTBE and the aqueous acid layer was separated. The acid layer was extracted with MTBE. The combined MTBE layer was washed with water followed by saturated NaHCO3 solution. The organic layer was washed with water until washings were neutral to pH paper. The organic layer was dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound.

Workup

  1. customfitted with an addition funnel and dry nitrogen inlet
  2. additionwere added fairly quickly
  3. stirringIt was stirred at between 6.9° C. and −5° C. for 1.5 h
  4. customThe reaction was quenched
  5. additionby slowly pouring into ice water
  6. additionMTBE was added
  7. stirringthe mixture was stirred well
  8. filtrationfiltered through Celite®
  9. washThe Celite® bed was washed with MTBE
  10. customthe aqueous acid layer was separated
  11. extractionThe acid layer was extracted with MTBE
  12. washThe combined MTBE layer was washed with water
  13. washThe organic layer was washed with water until washings
  14. dry with materialThe organic layer was dried over anhydrous Na2SO4
  15. filtrationfiltered
  16. customThe solvent was removed under reduced pressure
  17. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-72d9323ec4d14df7bf1e8c527e493b0e
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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