Dichloromethane → HCID 67549050, compound

HRID 1425047Notes

Reaction equation

HRID 1425047 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-912fc2a659994acf97be2699d5c0e6b9
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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