Benzenesulfonyl chloride, 2,4-dinitro- → HCID 86607837, compound

HRID 646706Notes

Reaction equation

HRID 646706 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C@@H:5]([NH2:7])[CH3:6].[N+:11]([C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[S:23](Cl)(=[O:25])=[O:24])([O-:13])=[O:12].C(N(CC)C(C)C)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:5]([NH:7][S:23]([C:15]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:14]=2[N+:11]([O-:13])=[O:12])(=[O:24])=[O:25])[CH3:6])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 74255Benzenesulfonyl chloride, 2,4-dinitro-HCID 81531DiisopropylethylamineHCID 9952938(S)-1-(3-bromophenyl)ethanamine

Product 1

HCID 86607837HCID 86607837, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred ice-cooled solution of (S)-(−)-3-bromo-α-methylbenzylamine (832 mg, 4.16 mmol, from Chiragene) in 15.6 mL of THF was added 1.33 g (4.99 mmol, 1.20 eq.) of 2,4-dinitrobenzenesulfonyl chloride, followed by 1.08 mL (6.20 mmol, 1.49 eq.) of N,N-diisopropylethylamine. The ice bath was removed, and the mixture was stirred at room temperature for 19 h and then concentrated. The residue was taken up in EtOAc, washed with 2×H2O, dried over Na2SO4, filtered, and concentrated. The residue was sonicated in ca. 5 mL of EtOAc until a precipitate was formed. The mixture was diluted to ca. 25 mL with hexanes. Filtration afforded product as a tan solid (1.69 g, 94.4% yield).

Workup

  1. customThe ice bath was removed
  2. concentrationconcentrated
  3. washwashed with 2×H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was sonicated in ca. 5 mL of EtOAc until a precipitate
  8. customwas formed
  9. filtrationFiltration

Sources & evidence

ORD record
ord-04e21450f35d4604a32ae155474de354
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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