Pyridine → HCID 22217877, compound

HRID 277727Notes

Reaction equation

HRID 277727 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[OH:15].N1C=CC=CC=1.C1C([N+]([O-])=O)=CC=C([Cl-][C:32]([O-])=[O:33])C=1>C(Cl)Cl>[C:8]([C:6]1[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]2[O:15][C:32](=[O:33])[NH:1][C:2]=2[CH:7]=1)([CH3:9])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 1049PyridineHCID 22217957HCID 22217957, compound

Product 1

HCID 22217877HCID 22217877, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-tert-butyl-6-nitrophenol (300 mg, 1.43 mmol) and pyridine (0.30 mL) in methylene chloride (30 mL) was added 4-nitrophenylchloroformate (280 mg, 1.39 mmol). The mixture was stirred for 24 h. The resulting solution was washed with aqueous sodium bicarbonate (2×20 mL), dried over solid magnesium sulfate and concentrated to an orange solid. Column chromatography (silica gel, eluant=40% EtOAc/petroleum ether) afforded 5-tert-butyl-7-nitro-3H-benzoxazol-2-one (70%).

Workup

  1. washThe resulting solution was washed with aqueous sodium bicarbonate (2×20 mL)
  2. dry with materialdried over solid magnesium sulfate
  3. concentrationconcentrated to an orange solid

Sources & evidence

ORD record
ord-2d202f2184c2483090d35359c6a2329d
Source dataset
uspto-grants-2002_03
Patent number
US06358945B1

Reaction notes

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