Water → HCID 14606696, compound

HRID 2099495Notes

Reaction equation

HRID 2099495 reaction equation
N12CCN(CC1)CC2.[Br:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][CH2:15][OH:16])=[CH:12][CH:11]=1.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].O>ClCCl>[CH3:26][C:25]1[CH:27]=[CH:28][C:22]([S:19]([O:16][CH2:15][CH2:14][C:13]2[CH:17]=[CH:18][C:10]([Br:9])=[CH:11][CH:12]=2)(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 14606696HCID 14606696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1,4-Diazabicyclo[2.2.2]octane (5.61 g, 0.050 mol) and 4-bromophenethyl alcohol (5.0 g, 0.025 mol) were combined in dichloromethane (100 mL). The resulting mixture was cooled to 0° C. in an ice bath and a solution of tosyl chloride (5.67 g, 0.029 mol) in dichloromethane (50 mL) was added via an addition funnel over 15 min. After stirring for about 1 h at 0° C., water (30 mL) was added and stirring was continued for another 30 min. The aqueous layer was then separated and discarded. The organic layer was dried (NaSO2), filtered, and concentrated under reduced pressure to give the title compound as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued for another 30 min
  3. customThe aqueous layer was then separated
  4. dry with materialThe organic layer was dried (NaSO2)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c117bf2b67fe494e937dfe48bfb38e04
Source dataset
uspto-grants-2009_08
Patent number
US07569586B2

Reaction notes

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