Dichloromethane → methyl N-(4-bromophenyl)-N-(3,5-dimethylbenzyl)oxamate

HRID 1363647Notes

Reaction equation

HRID 1363647 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[Br:8][C:9]1[CH:24]=[CH:23][C:12]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C.ClCCl>O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([N:13]([CH2:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=2)[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 598208394-bromo-N-(3,5-dimethylbenzyl)aniline

Product 1

HCID 59820918methyl N-(4-bromophenyl)-N-(3,5-dimethylbenzyl)oxamateYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl chloroglyoxylate (0.566 ml, 6.16 mmol) was added dropwise to a mixture of 4-bromo-N-(3,5-dimethylbenzyl)aniline (1.49 g, 5.13 mmol), triethylamine (1.08 ml, 7.70 mmol) and dichloromethane (20 ml) at 0°, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound (1.66 g, 86%) as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-e3ee85e4ccb849788b170a1d01244899
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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