4-Bromoaniline → HCID 58256459, compound

HRID 1967163Notes

Reaction equation

HRID 1967163 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]([S:17]([CH3:16])(=[O:19])=[O:18])[S:17]([CH3:16])(=[O:19])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 58256459HCID 58256459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-bromoaniline (500 mg, 2.91 mmol) and triethylamine (1215 μl, 8.72 mmol) were placed in a dry flask and dichloromethane (1.45 ml) was then added. The solution was cooled to 0° C. for 20 minutes. Methanesulfonyl chloride (226 μl, 2.91 mmol) was then added dropwise and the solution was allowed to warm to room temperature overnight. It was quenched with water and aqueous sodium bicarbonate, and extracted using ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification was conducted via silica gel chromatography (0-100% ethyl acetate in hexanes) to yield the title compound. 1H NMR (600 MHz, d6-DMSO): δ 7.63 (d, 2H), 7.38 (d, 2H), 3.42 (s, 6H).

Workup

  1. temperatureto warm to room temperature overnight
  2. customIt was quenched with water and aqueous sodium bicarbonate
  3. extractionextracted
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-9cb8e545713245f98555f22db3d31e56
Source dataset
uspto-grants-2013_04
Patent number
US08420695B2

Reaction notes

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