Benzenamine, 2-bromo-4-nitro- → 3-(2-Bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione

HRID 1437563Notes

Reaction equation

HRID 1437563 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=O)=[C:2]=[O:3].[Br:14][C:15]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:16]=1[NH2:17].CCN(C(C)C)C(C)C.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[Br:14][C:15]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:16]=1[N:17]1[C:6](=[O:8])[C:5]2[C:4](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:1][C:2]1=[O:3]

Participants

6

Reactant 4

HCID 25840Benzenamine, 2-bromo-4-nitro-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 519494Methyl 2-isocyanatobenzoate

Product 1

HCID 220644013-(2-Bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dioneYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-isocyanatobenzoate (0.266 g, 1.5 mmol) and 2-bromo-4-nitroaniline (0.325 g, 1.5 mmol) in DMF (2 mL) was added DIEA (0.79 mL). The reaction mixture was stirred at room temp for 24 hr, with addition of DBU (0.22 mL) at 17 hr. The reaction mixture was extracted with EtOAc, washed with 1 N HCl and brine, dried and concentrated to give crude product, which was chromatographed on silica gel with 10% EtOAc/CH2Cl2 to give 3-(2-bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione (0.24 g, 44%). ES-MS (M+H)+=362, 364 (Br).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washwashed with 1 N HCl and brine
  3. customdried
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customwas chromatographed on silica gel with 10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-3fa9b6b35921462c9b12a626a27b87cd
Source dataset
uspto-grants-2009_11
Patent number
US07622474B2

Reaction notes

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