Water → HCID 67438423, compound

HRID 1665026Notes

Reaction equation

HRID 1665026 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH2:7][NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30].O>ClCCl>[Br:1][C:2]1[O:6][C:5]([CH2:7][N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[S:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[Cl:22])(=[O:31])=[O:30])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 28428108HCID 28428108, compound

Product 1

HCID 67438423HCID 67438423, compoundYield 136%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the crude (5-bromo-furan-2-ylmethyl)-isobutyl-amine from step 1 (686 mg) in dichloromethane (8 mL) were added N,N-diisopropyl ethyl amine (686 mg) and 2-chlorobenzenesulfonylchloride (458 mg). The mixture was stirred for 18 h at r.t. Water was added and the mixture was extracted with dichloromethane. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 4:2) to give N-(5-bromo-furan-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide (1.2 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 4:2)

Sources & evidence

ORD record
ord-bc92519d6d884299b8db176deb9a1bbd
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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