Pyridine → HCID 43654432, compound

HRID 1591831Notes

Reaction equation

HRID 1591831 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:15][CH2:16][CH2:17][CH2:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:19]([CH2:18][CH2:17][CH2:16][Cl:15])(=[O:21])=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 78074-BromoanilineHCID 154103-Chloropropanesulphonyl chloride

Product 1

HCID 43654432HCID 43654432, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromoaniline (0.86 g, 5.0 mmol) was dissolved in CH2Cl2 (15 mL), pyridine (0.5 mL) was added, and 3-chloropropanesulfonyl chloride (0.6 mL, 5.0 mmol) was added. The mixture was stirred for 4 hours, diluted with ethyl acetate, and then washed with water, 2N HCl, brine, dried over MgSO4, and concentrated. The crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-60% ethyl acetate in hexane) to afford 1.2 g (77%) N-(4-bromophenyl)-3-chloropropane-1-sulfonamide.

Workup

  1. washwashed with water, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4d28705e4e464e3db9f3097137583003
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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