Triphenylphosphine → N-Methyl-N-(1-phenylbut-3-enyl)benzenesulfonamide

HRID 860163

Reaction equation

HRID 860163 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]1([CH:21](O)[CH2:22][CH:23]=[CH2:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:45][NH:46][S:47]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=[O:49])=[O:48]>C1COCC1.CCOCC.O>[CH3:45][N:46]([CH:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:22][CH:23]=[CH2:24])[S:47]([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)(=[O:48])=[O:49]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 78858N-MethylbenzenesulfonamideHCID 2201191-Phenylbut-3-en-1-olHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 69447982N-Methyl-N-(1-phenylbut-3-enyl)benzenesulfonamideYield 79.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

DIAD (9.0 mL, 45.9 mmol) was added dropwise over 10 min to a stirred solution of 1-phenyl-3-buten-1-ol (4.0 g, 27.0 mmol), PPh3 (10.6 g, 40.5 mmol) and N-methylphenylsulfonamide (6.0 g, 35.0 mmol) in THF (200 mL) under N2 and the resulting mixture was stirred at RT for 20 h. H2O (200 mL) and Et2O (200 mL) were added and separated. The organics were washed with brine (150 mL) and concentrated under reduced pressure while loading on to MgSO4. The mixture was then purified by column chromatography on silica eluting with 3% Et2O/iso-hexanes to yield the sulfonamide (6.45 g, 79%). 1H NMR (CDCl3, 360 MHz) δ 7.78 (2H, d, J=7.8 Hz), 7.53 (1H, t, J=7.8 Hz), 7.44 (2H, t, J=7.8 Hz), 7.30–7.18 (5H, m), 5.67–5.52 (1H, m), 5.20 (1H, t, J=7.8 Hz), 5.02 (1H, dd, J=17.1, 1.5 Hz), 4.93 (1H, dd, J=10.2, 1.3 Hz), 2.70 (1H, app. quintet, J=7.1 Hz), 2.65 (3H, s), 2.44 (1H, app. quintet, J=7.1 Hz).

Workup

  1. customseparated
  2. washThe organics were washed with brine (150 mL)
  3. concentrationconcentrated under reduced pressure while loading on to MgSO4
  4. customThe mixture was then purified by column chromatography on silica eluting with 3% Et2O/iso-hexanes

Sources & evidence

ORD record
ord-6349e2eb4bec40f69ec546faccdeb9ad
Source dataset
uspto-grants-2006_12
Patent number
US07153868B2

Linked notes

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