Triphenylphosphine → HCID 16753952, compound

HRID 1664126Notes

Reaction equation

HRID 1664126 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[S:12]([N:15]([CH3:17])[CH3:16])(=[O:13])=[O:14]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 16753951HCID 16753951, compound

Product 1

HCID 16753952HCID 16753952, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-azidomethyl-5-fluoro-N,N-dimethyl-benzenesulfonamide (660 mg, 2.6 mmol) in tetrahydrofuran (10 mL) and water (2 mL) was added triphenylphosphine (740 mg, 2.8 mmol), and the mixture stirred under nitrogen for 1 hr. The tetrahydrofuran was evaporated in vacuo and a mixture of the residue and 6N HCl (3 mL) in MeOH (5 mL) was heated at 80° C. for 20 hrs. This was washed with CH2Cl2, and the aqueous phase made basic with dilute NH4OH then extracted with CH2Cl2. The organic extract was dried (Na2SO4), filtered and concentrated to provide 210 mg (0.91 mmol, Yield 35%) of the title compound; 1H NMR (500 MHz, CDCl3) δ ppm: 2.84 (6H, s) 4.10 (2H, s) 7.23-7.29 (1H, m) 7.53-7.60 (2H, m); LC/MS m/z 233 (M+H).

Workup

  1. customThe tetrahydrofuran was evaporated in vacuo
  2. additiona mixture of the residue and 6N HCl (3 mL) in MeOH (5 mL)
  3. washThis was washed with CH2Cl2
  4. extractionthen extracted with CH2Cl2
  5. extractionThe organic extract
  6. dry with materialwas dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e6603ca86cec4b338a981b8c4252d1be
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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