Dabco → Benzylurea

HRID 2281976Notes

Reaction equation

HRID 2281976 reaction equation
O.NN.[CH2:4]([N:11]=[C:12]=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:14]12CCN(CC1)CC2.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:4]([NH:11][C:12]([NH2:14])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 9237DabcoHCID 24654Hydrazine hydrate (1:1)HCID 76639Benzyl isocyanateHCID 516892Sodium Bicarbonate

Product 1

HCID 10853Benzylurea

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound obtained in Example 190, (1) (87 mg) was dissolved in toluene (2 ml), and benzyl isocyanate (14 μl) was added to the solution. 1,4-Diazabicyclo-[2,2,2]octane (4.7 μl) was added to the mixture under ice cooling, and the resulting mixture was warmed to room temperature and stirred for 2 hours. Ethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the reaction mixture, the layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=20:1:0.1) to obtain a benzylurea compound (62 mg). (2) By using the compound obtained in (1) mentioned above (62 mg) as a starting material, a deprotected compound (55 mg) was obtained in the same manner as that of Example 2, (2). (3) By using the compound obtained in (2) mentioned above (55 mg) as a starting material, the compound shown in Table 5 (20 mg) was obtained in the same manner as that of Example 11.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=20:1:0.1)

Sources & evidence

ORD record
ord-4b56e87e76254649829e3f3a76a09735
Source dataset
uspto-grants-2015_09
Patent number
US09139609B2

Reaction notes

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