Triethylamine → HCID 22996533, compound

HRID 1167239Notes

Reaction equation

HRID 1167239 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH:8][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 533915p-Bromophenethylamine

Product 1

HCID 22996533HCID 22996533, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of of 4-bromophenethylamine (10.0 g, 50.0 mmol) and triethylamine (7.7 mL, 55.0 mmol) in 150 mL of dichloromethane was added dropwise methanesulfonyl chloride (4.3 mL 55.0 mmol) in 20 mL of dichloromethane. After two hours, the reaction mixture was washed once with 100 mL of 10% aqueous sodium bisulfate. The organic portion was separated and the aqueous portion was extracted three times with 50 mL each of dichloromethane. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford 14.0 g (100%) of the intermediate title compound.

Workup

  1. washthe reaction mixture was washed once with 100 mL of 10% aqueous sodium bisulfate
  2. customThe organic portion was separated
  3. extractionthe aqueous portion was extracted three times with 50 mL each of dichloromethane
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86ffe8d4b29949c3b9ef2b990ea910d9
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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