Chlorosulfonic acid → HCID 13504797, compound

HRID 1906422Notes

Reaction equation

HRID 1906422 reaction equation
ClS(O)(=O)=O.O[CH2:7][CH2:8][CH2:9][NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1>C(OCC)C>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18](/[CH:17]=[C:12]2/[CH:11]([N:10]3[CH2:9][CH2:8][CH2:7]3)[CH2:16][CH2:15][CH2:14][CH2:13]/2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 54489054HCID 54489054, compound

Product 1

HCID 13504797HCID 13504797, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
3 °C

Procedure

Chlorosulfonic acid was added dropwise during 7 min to a solution of N-(3-hydroxypropyl)-N-[2-(4-methoxyphenylmethylene)cyclohexyl]amine, 5 g (0.017 mole) in 325 ml of diethyl ether keeping the temperature at about 3° C. with cooling. The mixture was then stirred at this 3° C. temperature for 30 min and then at room temperature for 2 hr to ensure complete reaction. The resulting suspension was filtered and the solid washed with diethyl ether. The solid was added to a cold solution of 6.5 g of sodium hydroxide in 50 ml of water and the mixture was heated at 95° C. for 2 hr, then cooled in ice, saturated with solid sodium hydroxide and extracted with chloroform. The chloroform extract was dried with magnesium sulfate and evaporated. The residue was chromatographed on a Merck silica gel size C column using an 8% v/v methanol in chloroform solution containing 1% v/v ammonium hydroxide solution mixture as eluent. Elution of the residue loaded column with 560 ml of this mixture gave no material. The next 500 ml gave 0.41 g of (±)-(E)-1-[2-[(4-methoxyphenyl)methylene]cyclohexyl]azetidine as an oil. The NMR was consistent for this named product. A crystalline p-toluenesulfonate salt was prepared, mp 114°-115° C.

Workup

  1. temperaturewith cooling
  2. waitat room temperature for 2 hr to ensure complete
  3. customreaction
  4. filtrationThe resulting suspension was filtered
  5. washthe solid washed with diethyl ether
  6. additionThe solid was added to a cold solution of 6.5 g of sodium hydroxide in 50 ml of water
  7. temperaturethe mixture was heated at 95° C. for 2 hr
  8. temperaturecooled in ice, saturated with solid sodium hydroxide
  9. extractionextracted with chloroform
  10. extractionThe chloroform extract
  11. dry with materialwas dried with magnesium sulfate
  12. customevaporated
  13. customThe residue was chromatographed on a Merck silica gel size C column
  14. additioncontaining 1% v/v ammonium hydroxide solution mixture as eluent
  15. washElution of the residue loaded column with 560 ml of this mixture
  16. customgave no material

Sources & evidence

ORD record
ord-5c9eedd11834490587b806637f8e5b47
Source dataset
uspto-grants-1987_03
Patent number
US04652559

Reaction notes

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