Triethylamine → HCID 19804448, compound
Reaction equation
[S:1]1C=[CH:4][CH:3]=[C:2]1CC(O)=O.C([N:12]([CH2:15]C)[CH2:13][CH3:14])C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.Cl.[CH3:35][NH:36][OH:37].[NH4+].[Cl-]>C1C=CC=CC=1.O>[OH:37][N:36]([CH3:35])[C:15](=[O:24])[NH:12][CH2:13][C:14]1[S:1][CH:2]=[CH:3][CH:4]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a stirred solution of 2-thiopheneacetic acid (2.00 g, 14.1 mmol) in benzene (70 mL) was added triethylamine (1.424 g, 14.1 mmol) followed by diphenylphosphoryl azide (3.868 g, 14.1 mmol) and the mixture was heated at 90° C. for 1 hour. Then N-methylhydroxylamine hydrochloride (2.36 g, 28.2 mmol) was added as a solution in water (1 mL) containing triethylamine (2.85 g, 28.2 mmol) and the mixture was heated at 90° C. for 18 hours. The reaction was then poured into aqueous saturated NH4Cl (70 mL) and extracted with ethylacetate (3×70 mL). The combined organic extract was dried over MgSO4 and concentrated. The resulting residue was purified by column chromatography (silica gel, ether-hexanes, 1:1) followed by crystallization in ethylaCetate-hexanes and gave the desired product (467 mg).
Workup
- temperaturethe mixture was heated at 90° C. for 18 hours
- extractionextracted with ethylacetate (3×70 mL)
- extractionThe combined organic extract
- dry with materialwas dried over MgSO4
- concentrationconcentrated
- customThe resulting residue was purified by column chromatography (silica gel, ether-hexanes, 1:1)
- customfollowed by crystallization in ethylaCetate-hexanes
Sources & evidence
- ORD record
- ord-54add902c7f742409a474f80c99046e8
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05175183
Reaction notes
Loading…