Pyridine → N-(4-bromo-2-fluorophenyl)-3-chloropropane-1-sulfonamide

HRID 1453095Notes

Reaction equation

HRID 1453095 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[C:12]([F:17])[CH:11]=1.N1C=CC=CC=1>ClCCl>[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH:14][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])=[C:12]([F:17])[CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 43654020N-(4-bromo-2-fluorophenyl)-3-chloropropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chloropropane-1-sulfonyl chloride (3.16 ml, 0.026M) was added to a solution of 4-bromo-2-fluoroaniline (5.00 g, 0.026M) and pyridine (2.12 ml, 0.026M) in dichloromethane (100 ml) at 0° C. The reaction mixture was stirred for 1 hr, after which time it was partitioned between dichloromethane (100 ml) and 1N hydrochloric acid (100 ml). The organics were separated and dried over magnesium sulfate, filtered and concentrated in vacuuo to afford the title compound as a yellow oil (8.3 g). 1H NMR (CDCl3): δ 2.54 (m, 2H), 2.90 (m, 2H), 3.64 (d, J=2.56 Hz, 2H), 6.91 (d, J=3.56 Hz, 1H), 7.07 (m, 2H).

Workup

  1. customafter which time it was partitioned between dichloromethane (100 ml) and 1N hydrochloric acid (100 ml)
  2. customThe organics were separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-222ead6a57f3444e8433e9ae91852063
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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