Propargyl bromide → HCID 86692720, compound

HRID 2273345Notes

Reaction equation

HRID 2273345 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Br[CH2:15][C:16]#[CH:17].CCN(C(C)C)[CH:21]([CH3:23])[CH3:22]>C(#N)C>[CH2:15]([N:1]([CH2:23][C:21]#[CH:22])[CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=1)[C:16]#[CH:17]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 81531DiisopropylethylamineHCID 1696824-(2-Aminoethyl)benzenesulfonamide

Product 1

HCID 86692720HCID 86692720, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(2-aminoethyl)benzenesulfonamide (2.00 g, 10 mmol), 3-bromoprop-1-yne (2.16 mL, 20 mmol, 80% in toluene) in acetonitrile (50 mL) was added DIPEA (3.0 mL). The reaction mixtures were stirred at room temperature for overnight and concentrated under reduced pressure to give a residue. The residue was purified by biotage over silica gel eluting with DCM to 10% MeOH in DCM to afford 4-(2-(di(prop-2-yn-1-yl)amino)ethyl)benzenesulfonamide as a yellow oil (2.40 g, 87%). MS (ESI), 277.1 (M+H)+.

Workup

  1. customThe reaction mixtures
  2. concentrationconcentrated under reduced pressure
  3. customto give a residue
  4. customThe residue was purified by biotage over silica gel eluting with DCM to 10% MeOH in DCM

Sources & evidence

ORD record
ord-2df2ab768dea47deb0cc41f96dd55891
Source dataset
uspto-grants-2015_09
Patent number
US09120837B2

Reaction notes

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