1,8-Diazabicyclo(5.4.0)undec-7-ene → N-[2-(4-Bromophenyl)thiophen-3-yl]propane-2-sulfonamide

HRID 1994168Notes

Reaction equation

HRID 1994168 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[NH2:13])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[CH:25]([S:28](Cl)(=[O:30])=[O:29])([CH3:27])[CH3:26]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[NH:13][S:28]([CH:25]([CH3:27])[CH3:26])(=[O:30])=[O:29])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 534219992-(4-Bromophenyl)thiophen-3-amine

Product 1

HCID 53421842N-[2-(4-Bromophenyl)thiophen-3-yl]propane-2-sulfonamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add slowly to a solution of 2-(4-bromo-phenyl)-thiophen-3-yl amine(0.6 g, 2.36 mmol) in dry dichloromethane (10 mL) at 0° C., DBU 1.41 mL (9.45 mmol) and isopropylsulfonyl chloride (0.53 mL, 4.72 mmol) (Temp. always <0° C.). Remove the ice bath and stir the mixture at RT overnight. Add satd. aq. NH4Cl (10 mL) and extract the solution with EtOAc (2×10 mL). Dry the combined organic layers and concentrate under vacuum. Purify the crude residue by flash chromatography (Silica gel-Hexane/EtOAc 4:1) to give 0.8 g (94%) of propane-2-sulfonic acid [2-(4-bromo-phenyl)-thiophen -3-yl]-amide.

Workup

  1. customalways <0° C.
  2. customRemove the ice bath
  3. additionAdd satd
  4. extractionaq. NH4Cl (10 mL) and extract the solution with EtOAc (2×10 mL)
  5. customDry the combined organic layers
  6. concentrationconcentrate under vacuum
  7. customPurify the crude residue by flash chromatography (Silica gel-Hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-dff7044213b3412395a331714551c46e
Source dataset
uspto-grants-2010_01
Patent number
US07652064B2

Reaction notes

Loading…