Triethylamine → 5-Bromo-3,4-dihydro-3-methylquinazolin-2(1H)-one

HRID 459791Notes

Reaction equation

HRID 459791 reaction equation
[Br:1][C:2]1[C:3]([CH2:9][NH:10][CH3:11])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.ClC(Cl)(O[C:23](=[O:29])OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:9][N:10]([CH3:11])[C:23](=[O:29])[NH:8]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 184444723-Bromo-2-methylaminomethyl-phenylamine

Product 1

HCID 184445245-Bromo-3,4-dihydro-3-methylquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-2-methylaminomethyl-phenylamine (1.153 g, 5.36 mmol) in CH2Cl2 (50 ml) was added NEt3 (1.5 ml, 10.76 mmol), triphosgen (555 mg, 1.87 mmol) at 0° C. The reaction was allowed to warm up to room temperature and stirred overnight. After the solvent was removed by using a rotary evaporator, the residue was partitioned between water and ethyl acetate. The organic layer was washed by H2O and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by flash chromatography to give 5-bromo-3-methyl-3,4-dihydro-1H-quinazolin-2-one as white solid. (650 mg, 50%) MS: (M+H)+241.1.

Workup

  1. customAfter the solvent was removed
  2. customa rotary evaporator
  3. customthe residue was partitioned between water and ethyl acetate
  4. washThe organic layer was washed by H2O and brine
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe organic fraction was concentrated in vacuo
  7. customresulting brown residue
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-ef3d47313db143598ad2f5c41dde1193
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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