3-Chlorobenzoic Acid → 3-(4-Methylbenzene-1-sulfonyl)-6-oxa-3-azabicyclo[3.1.0]hexane

HRID 2302224Notes

Reaction equation

HRID 2302224 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][CH2:13][CH:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:24])C=1.ClC1C=C(C=CC=1)C(O)=O>ClCCl>[C:1]1([CH3:15])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:14][CH:13]3[CH:12]([O:24]3)[CH2:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 70297m-Chloroperbenzoic acidHCID 11746243HCID 11746243, compound

Product 1

HCID 184598483-(4-Methylbenzene-1-sulfonyl)-6-oxa-3-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

334.5 g (1.5 mol) of 1-(toluene-4-sulphonyl)-pyrroline are dissolved in 1.5 l of dichloromethane at room temperature and treated in the course of 15 minutes with a suspension of 408 g (about 1.65-1.77 mol) of 70-75% strength m-chloroperbenzoic acid in 900 ml of dichloromethane (cools during preparation). The mixture is heated under reflux for 16 hours (test for peroxide with KI/starch paper still indicates peroxide content), the suspension is cooled to 5° C., and the precipitated m-chlorobenzoic acid is, filtered off with suction and washed with 300 ml of dichloromethane (peroxide test with precipitate: negative; precipitate discarded). The filtrate is washed twice with 300 ml of 10% strength sodium sulphite solution in each case to destroy excess peroxide (test for peroxide is now negative), extracted with 300 ml of saturated sodium bicarbonate solution, washed with water, dried using sodium sulphate and concentrated to about a quarter of the volume. Test for peroxide again: negative. The mixture is concentrated and the solid residue is stirred with 400 ml of isopropanol with ice-cooling, and the precipitate is filtered off with suction and dried in vacuo at 70° C.

Workup

  1. temperatureThe mixture is heated
  2. filtrationfiltered off with suction
  3. washwashed with 300 ml of dichloromethane (peroxide test with precipitate: negative; precipitate discarded)
  4. washThe filtrate is washed twice with 300 ml of 10% strength sodium sulphite solution in each case
  5. customto destroy excess peroxide (test for peroxide
  6. extractionextracted with 300 ml of saturated sodium bicarbonate solution
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated to about a quarter of the volume
  10. concentrationThe mixture is concentrated
  11. temperaturecooling
  12. filtrationthe precipitate is filtered off with suction
  13. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-65a05cb029334bee87875512c01e1a8c
Source dataset
uspto-grants-2002_08
Patent number
US06432948B1

Reaction notes

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