Benzyl Bromide → HCID 86727482, compound

HRID 519105Notes

Reaction equation

HRID 519105 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]3[C:11]([CH2:12][O:13]2)=[N:10][NH:9][C:8](=[O:16])[CH:7]3[CH3:17])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].C([O-])([O-])=O.[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:27]([O:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]3[C:11]([CH2:12][O:13]2)=[N:10][NH:9][C:8](=[O:16])[CH:7]3[CH3:17])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86727480HCID 86727480, compound

Product 1

HCID 86727482HCID 86727482, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 7-hydroxy-4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.2 g, 0.72 mmol) and K2CO3 (0.30 g, 2.16 mmol) in DMF (10 mL) was added benzyl bromide (0.37 g, 2.16 mmol) dropwise. The solution was heated at 70° C. for 14 h. The reaction mixture was cooled to ambient temperature and brine (30 mL) was added. The aqueous phase was extracted with EtOAc (3×15 mL) and the combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether) to give 7-benzyloxy-4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.140 g, 53%) as yellow solid. 1H NMR (CDCl3, 400 MHz): δ 8.08 (s, 1H), 7.62 (s, 1H), 7.49 (m, 2H), 7.44 (m, 2H), 7.39 (m, 1H), 6.81 (s, 1H), 5.23 (s, 2H), 4.70 (m, 3H), 1.56 (d, J=6.8 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe aqueous phase was extracted with EtOAc (3×15 mL)
  3. dry with materialthe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-f1b17f485c3f428c85159ff0ef910590
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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