p-Bromobenzenesulfonyl chloride → 4-bromo-N-(tetrahydrofuran-2-ylmethyl)benzenesulfonamide

HRID 1710392Notes

Reaction equation

HRID 1710392 reaction equation
[CH2:1]([NH2:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.CCN(C(C)C)C(C)C>ClCCl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:7][CH2:1][CH:2]2[CH2:3][CH2:4][CH2:5][O:6]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 253298Tetrahydrofurfurylamine

Product 1

HCID 43396864-bromo-N-(tetrahydrofuran-2-ylmethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.70 ml of commercially available tetrahydrofurfurylamine are dissolved in 45 ml of dry dichloromethane. A solution of 3.83 g of 4-bromo-benzenesulfonyl chloride in 20 ml of dichloromethane are slowly added at room temperature. Subsequently, 5.14 ml of Hünig's base are added and stirring is continued for 1.5 hours. For extraction, the reaction mixture is diluted with 150 ml of dichloromethane and 50 ml of water. The organic layer is dried using Na2SO4, filtered with suction, and concentrated in vacuo. Purification by chromatography on flash silica gel (eluent: dichloromethane/0-5 vol. % ethanol) affords 4.33 g of the title compound as an light yellow oil. ESI-MS: 320.3/322.1 (MH+, 100%:98%). TLC: Rf=0.65 (dichloromethane/ethanol 20:1 parts by volume).

Workup

  1. extractionFor extraction
  2. additionthe reaction mixture is diluted with 150 ml of dichloromethane and 50 ml of water
  3. customThe organic layer is dried
  4. filtrationfiltered with suction
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on flash silica gel (eluent: dichloromethane/0-5 vol. % ethanol)

Sources & evidence

ORD record
ord-2196b413dc6d4385b2f53b8cff21aab5
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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