Methyl iodide → N-(5-tert-Butyl-1,2-oxazol-3-yl)-N,N',N'-trimethylurea
Reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([NH:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:8][N:7]=1)=[O:4].[H-].[Na+].[CH3:18]I>CN(C)C=O>[CH3:1][N:2]([CH3:15])[C:3]([N:5]([CH3:18])[C:6]1[CH:10]=[C:9]([C:11]([CH3:12])([CH3:14])[CH3:13])[O:8][N:7]=1)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1,1-dimethyl-3-(5-t-butyl-3-isoxazolyl)urea (10.99 g) in dry dimethylformamide (10 ml), 50% sodium hydride (2.75 g) is added at room temperature with stirring, and the resultant mixture is heated at 60° C. for 15 minutes. A solution of methyl iodide (8.86 g) in dry dimethylformamide (30 ml) is added at 10° C. in 1 hour thereto, and the mixture is heated at 80° C. for 5 minutes and evaporated to remove the solvent. The residue is combined with water and shaken with chloroform. The chloroform layer is dried over anhydrous sodium sulfate and the solvent is evaporated. The residue is chromatographed on a column of silica gel to give 1,1,3-trimethyl-3-(5-t-butyl-3-isoxazolyl)urea (10.94 g) as crystals melting at 90° to 91.0° C. The yield is 93.38%.
Workup
- customevaporated
- customto remove the solvent
- stirringshaken with chloroform
- dry with materialThe chloroform layer is dried over anhydrous sodium sulfate
- customthe solvent is evaporated
- customThe residue is chromatographed on a column of silica gel
Sources & evidence
- ORD record
- ord-eb5c0c2d06f248eeb2075f15043dc539
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04111680
Reaction notes
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