Water → HCID 67058885, compound

HRID 1665437Notes

Reaction equation

HRID 1665437 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH3:16])[CH2:12][C@H:13]1[CH2:15][O:14]1)(=[O:10])=[O:9].[CH3:17][C:18]([NH2:31])([CH3:30])[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1.Cl([O-])(=O)(=O)=O.[Li+].O>C(#N)C.[Cl-].[Na+].O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH2:12][C@H:13]([OH:14])[CH2:15][NH:31][C:18]([CH3:30])([CH3:17])[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[CH3:16])(=[O:10])=[O:9]

Participants

8

Reactant 4

HCID 962WaterHCID 15369616alpha,alpha-Dimethyl-2-naphthaleneethanamineHCID 23665649Lithium perchlorateHCID 86638430HCID 86638430, compound

Product 1

HCID 67058885HCID 67058885, compoundYield 78.7%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(S)-2-Bromo-N-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide (Exp. 1-1, 3.06 g) was dissolved in acetonitrile (25 mL), 2-methyl-1-(naphthalen-2-yl)propan-2-amine (am1, 1.99 g) and lithium perchlorate (KANTO, 1.06 g) were added thereto followed by reflux for 6 hours and 35 minutes. After cooling to room temperature, same amount of water and brine was added to the reaction solution and extraction was carried out with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to obtain the target compound (3.97 g).

Workup

  1. temperatureby reflux for 6 hours and 35 minutes
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f526a9871524de7a58edd9a35daee38
Source dataset
uspto-grants-2011_10
Patent number
US08039514B2

Reaction notes

Loading…