2-Amino-4-chlorophenol → HCID 86086750, compound

HRID 334544Notes

Reaction equation

HRID 334544 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

HCID 72652-Amino-4-chlorophenolHCID 57691793Methyl pent-4-ynimidate

Product 1

HCID 86086750HCID 86086750, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

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

  1. temperatureunder reflux
  2. customThe solvent was evaporated
  3. dissolutionthe residue was partly dissolved in MeOH
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe resulting crude residue was purified by flash chromatography (cyclohexane/AcOEt 9:1)

Sources & evidence

ORD record
ord-f20052d9fbb84bb68e49e1f0bd9dbc96
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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