N-bromobutanimide → HCID 18918385, compound

HRID 266744Notes

Reaction equation

HRID 266744 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:2][C:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:11])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18918246HCID 18918246, compound

Product 1

HCID 18918385HCID 18918385, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The product of step (i) (3.00 g) and N-bromosuccinimide (2.02 g) in carbon tetrachloride (50 ml) was heated at reflux temperature for 64 hours. The solvent was evaporated and the black residue dissolved in methanol/ethyl acetate, treated with charcoal, filtered and then evaporated. The resulting brown oil was purified by flash chromatography on silica, eluting with dichloromethane. Trituration with hexane gave methyl N-[4-(bromoacetyl)phenoxyacetyl]glycinate, 0.85 g, as a solid: mp softens 109°-111° C.; NMR (d6DMSO) δ 8.60 (1H, bt), 7.99 (2H, d), 7.09 (2H, d), 4.84 (2H, s), 4.69 (2H, s), 3.91 (2H, d), 3.64 (3H, s).

Workup

  1. temperatureat reflux temperature for 64 hours
  2. customThe solvent was evaporated
  3. dissolutionthe black residue dissolved in methanol/ethyl acetate
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting brown oil was purified by flash chromatography on silica
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-78d419e089ad42e29d93cae5fda0d579
Source dataset
uspto-grants-1997_07
Patent number
US05652242

Reaction notes

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