N-bromobutanimide → HCID 18918385, compound

HRID 743828Notes

Reaction equation

HRID 743828 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) δ8.60 (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-322a3f013edd4d3aaf816d242ab4c3b3
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Reaction notes

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