Water → HCID 70456182, compound

HRID 2164663Notes

Reaction equation

HRID 2164663 reaction equation
O.[O:2]=[C:3]1[CH:11]([Br:12])[CH2:10][CH2:9][C:8]2[N:7]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:6]=[CH:5][C:4]1=2.[Cl:22][CH2:23][CH:24](O)[CH2:25][OH:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:22][CH2:23][CH:24]1[CH2:25][O:26][C:3]2([CH:11]([Br:12])[CH2:10][CH2:9][C:8]3[N:7]([S:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)(=[O:15])=[O:14])[CH:6]=[CH:5][C:4]2=3)[O:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 72903-Chloro-1,2-propanediolHCID 521998p-Toluenesulfonic acid monohydrateHCID 13437712HCID 13437712, compound

Product 1

HCID 70456182HCID 70456182, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a three necked flask equipped with a thermometer, a stirrer and a reflux condenser having Widmer-type water trap filled with Molecular Sieves are placed 4-oxo-5-bromo-1-benzenesulfonyl-4,5,6,7-tetrahydroindole (100 parts), 3-chloro-1,2-propanediol (311 parts), p-toluenesulfonic acid monohydrate (3 parts) and toluene (4500 parts), and the mixture is refluxed for 7 hours 20 minutes while drying the refluxing azeotropic mixture. After cooling, the reaction mixture is adjusted to pH 9 with 2.5N aqueous sodium hydroxide with stirring, and the formed toluene layer is separated. The water layer is washed with benzene (200 parts). Toluene layer and benzene washing are combined, washed twice with water (500 parts) and dried over anhydrous sodium sulfate (500 parts). The drying agent is filtered off, and the filtrate is concentrated under reduced pressure. The obtained residue (143 parts) is dissolved in benzene (300 parts), stirred with active charcoal (50 parts) for 30 minutes and filtered through a filter-bed of siliceous earth. The filtrate is concentrated under reduced pressure, and stirring of resulted residue with a small amount of ether and hexane affords amorphous powder. This is collected by filtration, washed with a mixture of ether and hexane, and dried to give 4'-chloromethyl-5-bromo-1-benzenesulfonyl-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]-dioxolane diastereomer mixture (122 parts) in 97% yield.

Workup

  1. customIn a three necked flask equipped with a thermometer, a stirrer and a reflux condenser
  2. additionfilled with Molecular Sieves
  3. temperaturethe mixture is refluxed for 7 hours 20 minutes
  4. customwhile drying the refluxing azeotropic mixture
  5. temperatureAfter cooling
  6. customthe formed toluene layer is separated
  7. washThe water layer is washed with benzene (200 parts)
  8. washwashed twice with water (500 parts)
  9. dry with materialdried over anhydrous sodium sulfate (500 parts)
  10. filtrationThe drying agent is filtered off
  11. concentrationthe filtrate is concentrated under reduced pressure
  12. dissolutionThe obtained residue (143 parts) is dissolved in benzene (300 parts)
  13. stirringstirred with active charcoal (50 parts) for 30 minutes
  14. filtrationfiltered through
  15. filtrationa filter-bed of siliceous earth
  16. concentrationThe filtrate is concentrated under reduced pressure
  17. stirringstirring of resulted residue with a small amount of ether and hexane
  18. customaffords
  19. filtrationThis is collected by filtration
  20. washwashed with a mixture of ether and hexane
  21. customdried

Sources & evidence

ORD record
ord-9ac0ba7f81a941449907141957f312b0
Source dataset
uspto-grants-1985_03
Patent number
US04506079

Reaction notes

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