Propane sultone → HCID 11265767, compound

HRID 239723Notes

Reaction equation

HRID 239723 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[CH2:12]1[CH2:18][S:15](=[O:17])(=[O:16])[O:14][CH2:13]1>CC(C)=O>[CH2:1]([NH:11][CH2:13][CH2:12][CH2:18][S:15]([OH:17])(=[O:16])=[O:14])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 75799Benzo-1,3-dioxole-5-methylamine

Product 1

HCID 11265767HCID 11265767, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of piperonylamine (2.5 mL, 19.8 mmol) in acetone (30 mL) was added 1,3-propane sultone (2.52 g, 20.8 mmol). The mixture stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, washed with acetone (2×25 mL) and dried in vacuo. The product was suspended in 90% Acetone/MeOH (75 mL). The suspension was stirred at reflux for 30 sec., the solid was collected by filtration and dried in vacuo. This allowed the isolation of compound AW, 2.56 g (45%).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid material was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. customdried in vacuo
  5. stirringThe suspension was stirred
  6. temperatureat reflux for 30 sec
  7. filtration, the solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-bf0cd0c3e4af43cb91d7d497eb7fcf84
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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