N-bromobutanimide → HCID 18918385, compound

HRID 864832Notes

Reaction equation

HRID 864832 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-c0f0782e310f48f6b483f139c5c7f67a
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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