Triphenylphosphine → N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-N-(6-chloropyrid-2-yl)-methylsulfonamide

HRID 277127Notes

Reaction equation

HRID 277127 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[N:9]2[CH2:12][CH:11]([N:13](CC3C=CC=C(Cl)N=3)[SH:14](=[O:16])=[O:15])[CH2:10]2)=[CH:4][CH:3]=1.N(C(OCC)=O)=N[C:34](OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:63][C:64]1C=C[C:67]([CH:70](C2C=CC(Cl)=CC=2)[N:71]2CC(O)C2)=[CH:66][CH:65]=1.ClC1N=C(CNS(=O)=O)C=CC=1>O1CCCC1>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]2[CH2:10][CH:11]([N:13]([C:70]3[CH:67]=[CH:66][CH:65]=[C:64]([Cl:63])[N:71]=3)[S:14]([CH3:34])(=[O:15])=[O:16])[CH2:12]2)=[CH:30][CH:29]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 218966141-[Bis(4-chlorophenyl)methyl]azetidin-3-olHCID 178527238HCID 178527238, compoundHCID 178527239HCID 178527239, compound

Product 1

HCID 9935594N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-N-(6-chloropyrid-2-yl)-methylsulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

N-{1-[Bis-(4-chlorophenyl)methyl]azetidin-3-yl}-N-(6-chloropyrid-2-yl)methylsulfonamide may be prepared by carrying out the procedure in the following manner: 2.4 cm3 of diethyl azodicarboxylate and 1.44 g of triphenylphosphine are added, under argon, to a solution of 1.54 g of 1-[bis(4-chlorophenyl)methyl]-azetidin-3-ol and 1.22 g of N-(6-chloropyrid-2-yl)methylsulfonamide in 120 cm3 of anhydrous tetrahydrofuran. After stirring for 20 hours at 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.040-0.063 mm, height 30 cm, diameter 4.5 cm), eluting under an argon pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (80/20 by volume) and collecting 60-cm3 fractions. Fractions 6 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 1.75 g of N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-N-(6-chloropyrid-2-yl)-methylsulfonamide are obtained in the form of a white foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): from 2.85 to 3.00 (mt: 2H); 2.91 (s: 3H); 3.57 (split t, J=7 and 2 Hz: 2H); 4.25 (s: 1H); 4.64 (mt: 1H); from 7.20 to 7.35 (mt: 9H); 7.36 (dd, J=8 and 1 Hz: 1H); 7.71 (t, J=8 Hz: 1H)].

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customThe residue is chromatographed on a silica gel column (particle size 0.040-0.063 mm, height 30 cm, diameter 4.5 cm)
  3. washeluting under an argon pressure of 0.5 bar
  4. additionwith a mixture of cyclohexane and ethyl acetate (80/20 by volume)
  5. customcollecting 60-cm3 fractions
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-39fd1f60bd024f778eb7b951390d622f
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

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