Hydrochloric Acid → HCID 14071528, compound

HRID 1651872Notes

Reaction equation

HRID 1651872 reaction equation
CC([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:7]2)=O.[S].N1[CH2:29][CH2:28][O:27]CC1.Cl.[OH-:31].[K+]>O.C(O)C>[C:17]1([S:14]([NH:13][CH:8]2[CH2:7][C:6]3[C:10](=[CH:11][CH:12]=[C:4]([CH2:29][C:28]([OH:31])=[O:27])[CH:5]=3)[CH2:9]2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 14797Potassium HydroxideHCID 5362487SulfurHCID 14071500N-(5-Acetyl-2,3-dihydro-1H-inden-2-yl)benzenesulfonamide

Product 1

HCID 14071528HCID 14071528, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

8.3 g (26 mmol) of (2-benzenesulphonamido-indan-5-yl) methyl ketone, 2.1 g (65 mmol) of sulphur and 5.7 g (65 mmol) of morpholine are heated at 135° C. for 2 hours. Ice and hydrochloric acid are added and (2-benzenesulphonamido-indan-5-yl)-acetic acid thiomorpholide is extracted with ethyl acetate. It is purified by chromatography over silica gel using 8:2 ethylene chloride/ethyl acetate, which gives 10.6 g (97% of theory) in the form of a resin. The product is then heated under reflux for 2.5 hours with 10 g of potassium hydroxide in 100 ml of water and 40 ml of ethanol. The mixture is concentrated in vacuo, the alkaline phase is washed with methylene chloride, and the reaction product is precipitated by means of hydrochloric acid. It is recrystallised from isopropanol and from ethyl acetate/diisopropyl ether.

Workup

  1. extraction(2-benzenesulphonamido-indan-5-yl)-acetic acid thiomorpholide is extracted with ethyl acetate
  2. customIt is purified by chromatography over silica gel using 8:2 ethylene chloride/ethyl acetate, which
  3. customgives 10.6 g (97% of theory) in the form of a resin
  4. temperatureThe product is then heated
  5. concentrationThe mixture is concentrated in vacuo
  6. washthe alkaline phase is washed with methylene chloride
  7. customthe reaction product is precipitated by means of hydrochloric acid
  8. customIt is recrystallised from isopropanol and from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-70bfc79fe653479fbe653d5289c06ce3
Source dataset
uspto-grants-1990_05
Patent number
US04929754

Reaction notes

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