Sodium Azide → 3-Phenylisoxazole-5-carbonyl azide

HRID 409754Notes

Reaction equation

HRID 409754 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]([OH:14])=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(O[N:23]1[N:31]=[N:30]C2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N-]=[N+]=[N-].[Na+].CCN(C(C)C)C(C)C>CN(C=O)C.C1COCC1>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]([N:30]=[N+:31]=[N-:23])=[O:14])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 81531DiisopropylethylamineHCID 7374743-Phenylisoxazole-5-carboxylic AcidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 579476213-Phenylisoxazole-5-carbonyl azideYield 60.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-phenylisoxazole-5-carboxylic acid (1.0 g, 5 mmol, 1.0 equiv.) in DMF (20 mL) and THF (20 mL), was added HBTU (2.28 g, 6 mmol, 1.2 equiv.), followed by sodium azide (0.65 g, 10 mmol, 2.0 equiv.) and DIEA (2.6 mL, 15 mmol, 3.0 equiv.). The mixture was stirred at RT for 30 min, concentrated, followed by adding of H2O (40 mL). The precipitate was filtered, washed with H2O, and dried in vacuo to give 3-phenylisoxazole-5-carbonyl azide (0.65 g, 60%). LRMS (M−18H+) m/z 187.1.

Workup

  1. concentrationconcentrated
  2. additionby adding of H2O (40 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1de94b21b2bc4960b8b8ceecada599d5
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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