Potassium Carbonate → HCID 16769580, compound

HRID 2089524Notes

Reaction equation

HRID 2089524 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]([CH3:13])[C:6]([CH2:8][O:9]C(=O)C)=[O:7].C(=O)([O-])[O-].[K+].[K+]>CO.O>[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]([CH3:13])[C:6](=[O:7])[CH2:8][OH:9]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59199343HCID 59199343, compound

Product 1

HCID 16769580HCID 16769580, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of acetic acid [(2-bromo-benzyl)-methyl-carbamoyl]-methyl ester (11.0 g, 36.8 mmol) in methanol (250 mL) is added a solution of potassium carbonate (7.63 g, 55.2 mmol) in water (45 mL). After stirring for 90 minutes the reaction is concentrated to near dryness and then dissolved in dichloromethane. The resulting solution is washed with brine, dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 1:99 to 3:47) to furnish N-(2-bromo-benzyl)-2-hydroxy-N-methyl-acetamide; MS: (ESI) m/z 258.1, 260.1 (M+H)+.

Workup

  1. concentrationis concentrated
  2. dissolutiondissolved in dichloromethane
  3. washThe resulting solution is washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 1:99 to 3:47)

Sources & evidence

ORD record
ord-ed316ff8b1b24ac08c5b667478bcd2b0
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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