Sodium hydride → 2-(5-Amino-2-methyl-phenylamino)-oxazole-5-carboxylic acid methyl ester
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])C)[CH:7]=1.[H-].[Na+].[CH3:15][O:16][C:17]([C:19]1OC(Cl)=[N:21][CH:20]=1)=[O:18]>C1COCC1>[CH3:15][O:16][C:17]([C:19]1[O:11][C:9]([NH:8][C:6]2[CH:7]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=2[CH3:12])=[N:21][CH:20]=1)=[O:18]Participants
Procedure
A solution of N-(5-Amino-2-methyl-phenyl)-acetamide (0.51 g, 3.1 mmol) in THF (12 mL) was added to a suspension of NaH (186 mg, 4.65 mmol, 60% dispersion in mineral oil) in THF (12 mL) at 0° C. under an atmosphere of argon. The mixture was stirred for 30 min. at room temperature and cooled to 0° C. A solution of 2-chloro-oxazole-5-carboxylic acid methyl ester (0.5 g, 3.1 mmol) in THF (12 mL) was added dropwise to the mixture. After 30 min., at 0° C., the reaction was poured into ice water (30 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and filtered. After removal of solvent the residue was silica gel column chromatographed (CH2Cl2/Ethanol:99/1) to give 0.54 g of 2-(5-Amino-2-methyl-phenylamino)-oxazole-5-carboxylic acid methyl ester (71%) as a Colorless syrup.
Workup
- temperaturecooled to 0° C
- waitAfter 30 min.
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customAfter removal of solvent the residue
- customchromatographed (CH2Cl2/Ethanol:99/1)
Sources & evidence
- ORD record
- ord-de5f8c4a62c24727a9023a5b404e1123
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08080669B2
Reaction notes
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