p-Toluenesulfonic acid → 7-Iodo-8-phenyl-chromeno[7,8-d]oxazol-6-one

HRID 1037378Notes

Reaction equation

HRID 1037378 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([I:19])=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1>COC(OC)OC>[I:19][C:7]1[C:6](=[O:20])[C:5]2[CH:4]=[CH:3][C:2]3[N:1]=[CH:21][O:12][C:11]=3[C:10]=2[O:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 670679197-Amino-8-hydroxy-3-iodo-2-phenyl-chromen-4-one

Product 1

HCID 670680127-Iodo-8-phenyl-chromeno[7,8-d]oxazol-6-oneYield 3,494.8%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-amino-8-hydroxy-3-iodo-2-phenyl-chromen-4-one (151 mg, 0.4 mmol) in trimethylorthoformate (3 mL) was added p-toluenesulfonic acid (2 mg, 0.01 mmol). The reaction mixture was stirred at 100° C. for 2 hours, allowed to RT and the solvent removed. The resulting residue was subjected to flash chromatography (SiO2, gradient 20-100% ethyl acetate in cyclohexane) to give the title compound as a beige solid (136 mg, 87%). LCMS (Method G): RT=3.52 min, [M+H]+=389.

Workup

  1. customallowed to RT
  2. customthe solvent removed

Sources & evidence

ORD record
ord-d9a507bb1f2d4a0ab174aec6b27b482e
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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