N-Methoxy-N,2,4-trimethylthiazole-5-carboxamide → (4-Chlorophenyl)(2,4-dimethylthiazol-5-yl)methanone
Reaction equation
CON(C)[C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[CH3:12])=[O:5].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Cl)=[CH:17][CH:16]=1>C1COCC1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:4]([C:6]2[S:10][C:9]([CH3:11])=[N:8][C:7]=2[CH3:12])=[O:5])=[CH:17][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a flask containing N-methoxy-N,2,4-trimethylthiazole-5-carboxamide (510 mg, 2.55 mmol, Intermediate 17: step a) was added THF (18 mL) and the solution was cooled to 0° C. To this solution was added (4-chlorophenyl)magnesium chloride (1 M in diethylether, 3.3 mL, 3.3 mmol). A homogeneous yellow mixture resulted and was allowed to warm to room temperature over 15 minutes. After 2 hours, the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc (4×50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to dryness. Chromatography on silica gel (100% DCM increasing to 10% EtOAc-DCM) provided the title compound as a white solid.
Workup
- customA homogeneous yellow mixture resulted
- temperatureto warm to room temperature over 15 minutes
- customthe reaction mixture was quenched with aqueous NH4Cl solution
- extractionthe aqueous portion was extracted with EtOAc (4×50 mL)
- washThe combined organics were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-ffcb2083080b4494b6c78383daef645e
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403816B2
Reaction notes
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