Toluene → HCID 69120849, compound

HRID 1043878Notes

Reaction equation

HRID 1043878 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]([O:16][C:17]([CH3:20])(C)C)(=[O:15])[NH:13][NH2:14].[C:21]1(C)C=CC=C[CH:22]=1>>[O:11]=[C:1]1[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:6])[N:14]1[NH:13][C:12](=[O:15])[O:16][CH2:17][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 1140TolueneHCID 6811Phthalic AnhydrideHCID 70091tert-Butyl carbazate

Product 1

HCID 69120849HCID 69120849, compound

Procedure

A suspension of phthalic anhydride (30.0 g) and t-butyl carbazate (CAS No. 870-46-2) (26.8 g) in toluene (600 mL) was azeotropically refluxed using a Dean-Stark trap for 3.25 hours. The insoluble matter was removed by hot filtration. The filtrate was concentrated to about one-third volume under reduced pressure and then ice-cooled. The precipitated solid was collected by filtration. The resulting solid was dissolved in ethyl acetate (750 mL) and purified by short path NH silica gel column chromatography (100% ethyl acetate). The target fraction was concentrated, and the residue was then triturated with ethyl acetate (20 mL). The resulting solid was collected by filtration and dried under reduced pressure to give the title compound (16.4 g).

Workup

  1. customfor 3.25 hours
  2. customThe insoluble matter was removed by hot filtration
  3. concentrationThe filtrate was concentrated to about one-third volume under reduced pressure
  4. temperatureice-cooled
  5. filtrationThe precipitated solid was collected by filtration
  6. dissolutionThe resulting solid was dissolved in ethyl acetate (750 mL)
  7. custompurified by short path NH silica gel column chromatography (100% ethyl acetate)
  8. concentrationThe target fraction was concentrated
  9. customthe residue was then triturated with ethyl acetate (20 mL)
  10. filtrationThe resulting solid was collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-94a79a3d9618431eb3afb452b80d375f
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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