Methane → Benzenesulfonamide, 3-[4-[(6-bromohexyl)oxy]butyl]-

HRID 749233

Reaction equation

HRID 749233 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.C>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([S:19]([NH2:22])(=[O:20])=[O:21])[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 297MethaneHCID 218955583-[4-[(6-Bromohexyl)oxy]but-1-ynyl}benzenesulfonamide

Product 1

HCID 21895438Benzenesulfonamide, 3-[4-[(6-bromohexyl)oxy]butyl]-Yield 78.8%

Conditions

Temperature
20 °C

Procedure

3-{4-[(6-Bromohexyl)oxy]but-1-ynyl}benzenesulfonamide (627 g) in IMS (1900 ml) was stirred with activated charcoal (314 g) at room temperature for 2 h and then filtered through a short pad of Celite. The filter pad was washed with IMS (4300 ml) and the filtrate transferred to a hydrogenation vessel. 5% Platinum on Charcoal (520.1 g, ˜50% water) was added and the reaction mixture was then stirred under an atmosphere of hydrogen (0.2 bar) at 20° C. for 6 h. The mixture was then filtered through a short pad of Celite and concentrated under reduced pressure to give the title compound (499 g) as a solid, LC RT=5.66 min.

Workup

  1. filtrationfiltered through a short pad of Celite
  2. washThe filter pad was washed with IMS (4300 ml)
  3. customthe filtrate transferred to a hydrogenation vessel
  4. addition5% Platinum on Charcoal (520.1 g, ˜50% water) was added
  5. filtrationThe mixture was then filtered through a short pad of Celite
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26fdd124fc37462598b2657b088290bc
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Linked notes

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