Benzyl Bromide → HCID 59655008, compound

HRID 2053448Notes

Reaction equation

HRID 2053448 reaction equation
[Cl:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:22]1[CH2:32][CH2:31]N2[C:25](=NCCC2)[CH2:24][CH2:23]1.CCOC(C)=O>CC#N>[CH2:10]([O:9][C:7](=[O:8])[C:6]1[CH:13]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[NH:11][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 784805-Chloroisatoic anhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 59655008HCID 59655008, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-chloroisatoic anhydride (5.00 g, 25.3 mmol) and benzylbromide (78.83 g, 50.6 mmol) in 50 ml of CH3CN was added 7.57 ml of DBU (50.6 mmol) at rt under Ar. The resulting mixture was stirred at rt for 16 hr. Treated with 100 ml of EtOAc, the mixture was washed with H2O, brine and dried (Na2SO4). Removal of the solvent in vacuo followed by flash chromatography of the residue on silica gel (10% DCM/hexanes-5% EtOAc/hexanes) gave 6.50 g (73%) of product as a brown oil.: 1H-NMR (CDCl3; 400 MHz) 3 8.17 (t, 1H, J=5.2 Hz), 7.92 (d, 1H, J=2.8 Hz), 7.19-7.48 (m, 11H), 6.56 (d, 1H, J=9.2 Hz), 5.31 (s, 2H), 4.43 (d, 2H, J=5.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C21H18ClNO2, 352.1 (M+H), found 352.0.

Workup

  1. washthe mixture was washed with H2O, brine
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-bcbe5cd537c94e7a835ee5ae8e8ae63d
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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