Triethylamine → 2-Methyl-3-(4-phenyl-thiophen-2-yl)-acryloyl azide

HRID 1505636Notes

Reaction equation

HRID 1505636 reaction equation
[CH3:1]/[C:2](=[CH:6]\[C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:11]=1)/[C:3](O)=[O:4].C(N(CC)CC)C.C1(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[CH3:1][C:2](=[CH:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:11]=1)[C:3]([N:39]=[N+:40]=[N-:41])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 66671279(E)-2-Methyl-3-(4-phenyl-thiophen-2-yl)-acrylic acid

Product 1

HCID 866135582-Methyl-3-(4-phenyl-thiophen-2-yl)-acryloyl azide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-2-methyl-3-(4-phenyl-thiophen-2-yl)-acrylic acid (924 mg, 3.78 mmol) and triethylamine (617 μl, 4.43 mmol) in THF (10 ml) was added diphenylphosphoryl azide (897 μl, 6.27 mmol) at 0° C. The reaction was next stirred for 4 h at room temperature. At which point the contents of the reaction flask were partitioned between ethyl acetate (25 ml) and sodium hydrogencarbonate (25 ml). The organic phase was separated and the solvent removed in vacuo. The crude residue was suspended between methanol (25 ml) and distilled water (25 ml), the precipitate collected and dried (MgSO4) to afford the title compound as a white solid.

Workup

  1. customAt which point the contents of the reaction flask were partitioned between ethyl acetate (25 ml) and sodium hydrogencarbonate (25 ml)
  2. customThe organic phase was separated
  3. customthe solvent removed in vacuo
  4. distillationdistilled water (25 ml)
  5. customthe precipitate collected
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-4af747dd6cfd4d708da4582e1a13010c
Source dataset
uspto-grants-2015_12
Patent number
US09216992B2

Reaction notes

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