Diisopropylethylamine → HCID 178510658, compound
Reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N:7]=[C:8]=[O:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:32][CH:33]([C:36]#[N:37])[C:34]#[N:35]>O1CCCC1>[NH2:37][C:36]1[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:11][CH:10]=2)[C:8]([OH:9])=[N:32][C:33]=1[C:34]#[N:35]Participants
Procedure
4-Fluorobenzylisocyanate (1.37 g, 10 mmol) and N,N-diisopropylethylamine (1.29 g, 10 mmol) were added to aminomalononitrile p-toluenesulfonate (2.53 g, 10 mmol) suspended in tetrahydrofuran (50 ml). The mixture was stirred at room temperature for 24 hours and then the solvent was removed in vacuo. To the residue was added ethyl acetate and the solution was washed and the organic layer was extracted with 1N aqueous sodium hydroxide. The extract was neutralized with 10% aqueous potassium hydrogen sulfide and extracted with ethyl acetate. The organic layer was dried on sodium sulfate and the solvent was removed in vacuo. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (1.93 g, yield 89%).
Workup
- customthe solvent was removed in vacuo
- additionTo the residue was added ethyl acetate
- washthe solution was washed
- extractionthe organic layer was extracted with 1N aqueous sodium hydroxide
- extractionextracted with ethyl acetate
- customThe organic layer was dried on sodium sulfate
- customthe solvent was removed in vacuo
- customThe residue was purified with silica gel chromatography (1% methanol/chloroform)
Sources & evidence
- ORD record
- ord-6dde8f5f8374423b892db3a5e9cd17a3
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06329381B1
Reaction notes
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