Hydrogen Bromide → HCID 19426286, compound

HRID 742536Notes

Reaction equation

HRID 742536 reaction equation
C1(C)C=C[C:4]([S:7]([N:10]2[CH2:18][CH2:17][N:16](S(C)(=O)=O)[CH2:15][CH2:14][N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][CH2:11]2)(=[O:9])=[O:8])=CC=1.Br>C(O)(=O)C>[CH3:4][S:7]([N:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19426280HCID 19426280, compound

Product 1

HCID 19426286HCID 19426286, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1,4,-bis-(p-toluenesulfonyl)-7-methanesulfonyl-1,4,7-triazacyclononane (38.8 g, 0.08 mol) 800 mL of glacial acetic acid and 150 mL of 48% hydrobromic acid was refluxed for 72 hours. The reaction solution was cooled to 25 C. and most of the solvents were removed under reduced pressure. Then 50 mL of 48% hydrobromic acid were added and the solvents were again evaporated. This procedure was repeated two more times to remove acetic acid. A mixture of 100 mL of absolute ethanol and 200 mL of diethyl ether was added and the solids were filtered. The solids were combined with sodium hydroxide pellets (18.0 g, 0.45 mol) in 250 mL of toluene and the mixture was refluxed for 15 hours. The remaining solid was filtered and washed with 75 mL of hot toluene. The filtrate was concentrated to a volume of 60 mL and allowed to cool slowly to 25 C. The colorless crystals were filtered and dried to give 1-methanesulfonyl-1,4,7-triazacyclononane (11.1 g, 0.05 mol, 71%).

Workup

  1. temperaturewas refluxed for 72 hours
  2. temperatureThe reaction solution was cooled to 25 C
  3. customand most of the solvents were removed under reduced pressure
  4. additionThen 50 mL of 48% hydrobromic acid were added
  5. customthe solvents were again evaporated
  6. customto remove acetic acid
  7. additionA mixture of 100 mL of absolute ethanol and 200 mL of diethyl ether
  8. additionwas added
  9. filtrationthe solids were filtered
  10. temperaturethe mixture was refluxed for 15 hours
  11. filtrationThe remaining solid was filtered
  12. washwashed with 75 mL of hot toluene
  13. concentrationThe filtrate was concentrated to a volume of 60 mL
  14. temperatureto cool slowly to 25 C
  15. filtrationThe colorless crystals were filtered
  16. customdried

Sources & evidence

ORD record
ord-203097ff49fb417cab1ee9ece3b3135c
Source dataset
uspto-grants-1996_09
Patent number
US05554749

Reaction notes

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