Oxalyl chloride → Flurbiprofen

HRID 1805400Notes

Reaction equation

HRID 1805400 reaction equation
[CH3:1][CH:2]([C:16](N)=[O:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([F:15])[CH:4]=1.C(Cl)(=O)C(Cl)=[O:21]>C(Cl)Cl.ClCCCl>[CH3:1][CH:2]([C:16]([OH:17])=[O:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([F:15])[CH:4]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 9837706HCID 9837706, compound

Product 1

HCID 3394Flurbiprofen

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of flurbiprofen amide (3.0 g, 12.33 mmol) in DCM (70 mL) was added oxalyl chloride (1.87 g, 14.79 mmol) at 0° C. and refluxed for 16 h. Reaction mixture was cooled to RT and treated with LI-2b (2.45 g, 12.33 mmol) in DCE (10 mL) and stirred overnight. After usual aqueous work-up and chromatographic purification, 0.5 g of I-C1-NOPD14a were obtained. 1H NMR (CDCl3, 300 MHz): δ 1.55 (d, 3H, J=6.9 Hz), 2.94-2.97 (bs, 4H), 4.38-4.47 (bs, 3H), 4.68 (t, 2H, J=6.6 Hz), 7.13-7.55 (bs, 8H) MS: ES+ m/z 469.03 [M+H]+, 467.16 [M−H]+.

Workup

  1. temperaturerefluxed for 16 h
  2. customReaction mixture
  3. customAfter usual aqueous work-up and chromatographic purification, 0.5 g of I-C1-NOPD14a
  4. customwere obtained

Sources & evidence

ORD record
ord-38d7a109a6d5457abc7155bbb51a4b66
Source dataset
uspto-grants-2013_01
Patent number
US08354455B2

Reaction notes

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