2-Amino-4-chlorophenol → HCID 86086750, compound
Reaction equation
[CH3:1][O:2][C:3](=[NH:8])[CH2:4][CH2:5][C:6]#[CH:7].N[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12]C=1O>ClC(Cl)C>[CH2:4]([C:3]1[O:2][C:1]2[CH:10]=[CH:15][C:14]([Cl:16])=[CH:13][C:12]=2[N:8]=1)[CH2:5][C:6]#[CH:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of pent-4-ynimidic acid methyl ester (142 mg, 1.28 mmol) and 2-amino-4-chlorophenol (227 mg, 1.53 mmol) in dichloroethane (10 mL) was stirred for 2 days under reflux. The solvent was evaporated, the residue was partly dissolved in MeOH and filtered. The filtrate was concentrated, and the resulting crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1) to yield 18 mg (87 μmol, 7%) of 2-(but-3-ynyl)-5-chlorobenzo[d]oxazole.
Workup
- temperatureunder reflux
- customThe solvent was evaporated
- dissolutionthe residue was partly dissolved in MeOH
- filtrationfiltered
- concentrationThe filtrate was concentrated
- customthe resulting crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1)
Sources & evidence
- ORD record
- ord-275d77ccbccc49b99777bc75c38a400b
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08674106B2
Reaction notes
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