Sodium Carbonate → 1-Bromocyclopropanecarboxylic acid-1,1-dimethyl-2-hydroxy-ethylamide

HRID 478159Notes

Reaction equation

HRID 478159 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].C(=O)([O-])[O-].[Na+].[Na+].[Br:13][C:14]1([C:17](Cl)=[O:18])[CH2:16][CH2:15]1.[OH-].[Na+]>O.C(Cl)Cl>[CH3:5][C:2]([NH:1][C:17]([C:14]1([Br:13])[CH2:16][CH2:15]1)=[O:18])([CH3:6])[CH2:3][OH:4]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 118072-Amino-2-methyl-1-propanolHCID 14798Sodium HydroxideHCID 109102061-Bromocyclopropane-carboxylic acid chloride

Product 1

HCID 180008711-Bromocyclopropanecarboxylic acid-1,1-dimethyl-2-hydroxy-ethylamideYield 85.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.69 g of 2-amino-2-methyl-1-propanol is introduced into 85 ml of methylene chloride under nitrogen at room temperature, and 2.38 g of sodium carbonate is added to 38 ml of water and then 3.6 g of acid chloride 107. It is stirred overnight at room temperature and then treated with methanolic 2N sodium hydroxide solution. The organic phase is separated, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 3.83 g of 1-bromocyclopropanecarboxylic acid-1,1-dimethyl-2-hydroxy-ethylamide 108 is obtained as a colorless oil.

Workup

  1. customThe organic phase is separated
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-cfb2f46a2f3f457783c38397b4d01559
Source dataset
uspto-grants-2003_11
Patent number
US06642218B2

Reaction notes

Loading…