Triethylamine → HCID 3817108, compound

HRID 392449Notes

Reaction equation

HRID 392449 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([NH2:8])[CH3:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:18]([S:20](Cl)(=[O:22])=[O:21])[CH3:19]>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([NH:8][S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])[CH3:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 911751-(4-Bromophenyl)ethylamine

Product 1

HCID 3817108HCID 3817108, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-α-methylbenzylamine (8.15 g, 40.73 mmol) and (4.15 g, 41.00 mmol) triethylamine dissolved in 150 ml dichloromethane was treated slowly with ethanesulfonyl chloride (5.27 g, 41.00 mmol) and stirred for 15 minutes. The reaction mixture was extracted with 50 ml 1N HCl/15 ml brine. The organic layer was separated, dried sodium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR: 7.52 (d,2H,J=12 Hz), 7.25 (d,2H,J=12 Hz), 4.77 (m,1H), 4.63 (m,1H), 2.77 (m,2H), 1.56 (d,3H,J=8 Hz), 1.27 (t,3H,J=8 Hz). MS calcd. 292.2; MS (M+−1) 291.1.

Workup

  1. extractionThe reaction mixture was extracted with 50 ml 1N HCl/15 ml brine
  2. customThe organic layer was separated
  3. filtrationdried sodium sulfate, filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c96892e40af43a3ac720b4a93b67c9a
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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