Benzyl Bromide → HCID 86587245, compound

HRID 605884Notes

Reaction equation

HRID 605884 reaction equation
[OH:1][C:2]1[NH:3][C:4](=[O:16])[C:5]2[C:14]([CH:15]=1)=[N:13][CH:12]=[C:11]1[C:6]=2[CH:7]=[CH:8][CH:9]=[CH:10]1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([O:1][C:2]1[NH:3][C:4](=[O:16])[C:5]2[C:14]([CH:15]=1)=[N:13][CH:12]=[C:11]1[C:6]=2[CH:7]=[CH:8][CH:9]=[CH:10]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178518722HCID 178518722, compound

Product 1

HCID 86587245HCID 86587245, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The hydrobromide salt 4d (100 mg, 0.34 mmol) was dissolved in 3 mL DMF. Potassium carbonate (100 mg) and benzyl bromide (60 μL, 0.50 mmol) were added to the solution and the mixture was heated to 60° C. for 14 h. The solvent was removed in vacuo and the residue was washed with water (5 mL) and boiling MeOH (10 mL) and filtered. The solid 4e (47 mg, 46%) was pure while the filtrate contained a mixture of isomers. Mp=271-276° C. 1H NMR (d6-DMSO) δ 11.68 (bs, 1H), 8.71 (d, 1H), 8.30 (d, 1H), 7.93 (t, 1H), 7.74 (m, 2H), 7.55 (d, 2H), 7.40 (t, 2H), 7.32 (t, 1H), 7.09 (d, 1H), 5.54 (s, 2H). Anal Calcd. for C19H14N2O2(H2O): C, 71.24; H, 5.03; N, 8.74. Found: C, 71.28; H, 4.83; N, 8.38.

Workup

  1. customThe solvent was removed in vacuo
  2. washthe residue was washed with water (5 mL)
  3. filtrationfiltered
  4. additiona mixture of isomers

Sources & evidence

ORD record
ord-8c3a0b2ea7f8499e8460e08e6387a0e8
Source dataset
uspto-grants-2011_03
Patent number
US07915280B2

Reaction notes

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