Dichloromethane → HCID 67549050, compound

HRID 43571Notes

Reaction equation

HRID 43571 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH2:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].BrN1C(=O)CCC1=O.C(OCC)(=O)C.ClCCl>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:11][CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[N:14]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 10857878HCID 10857878, compound

Product 1

HCID 67549050HCID 67549050, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

α,α-Bisisobutyronitrile (66 mg, 0.4 mmol) was added to a solution of methyl 2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate (described in Kline, Toni; Andersen, Niels H.; Harwood, Eric A.; Bowman, Jason; Malanda, Andre; Endsley, Stephanie; Erwin, Alice L.; Doyle, Michael; Fong, Susan; Harris, Alex L.; Mendelsohn, Brian; et al., J. Med. Chem., 45, 14, 2002, 3112-3129, 1.95 g, 7.8 mmol) in benzene (30 mL). The mixture was heated to 80° C. and N-bromosuccinimide (1.53 g, 8.58 mmol) was added. The mixture was stirred at the same temperature for 1.5 hours and then ethyl acetate and dichloromethane were added, followed by sequentially washing with water and brine. This was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=100/0, 20/1, 10/1) to obtain 1.29 g of the title compound as a colorless solid (67%).

Workup

  1. washby sequentially washing with water and brine
  2. dry with materialThis was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=100/0, 20/1, 10/1)

Sources & evidence

ORD record
ord-980fb99caa0242cb8a9f2d422ce3347c
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…