Ethyl bromoacetate → HCID 15572227, compound

HRID 2059277Notes

Reaction equation

HRID 2059277 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:19]([O:18][C:16]([CH2:15][NH:6][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:11]([CH3:13])[CH3:12])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 32484DiisopropylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 15572227HCID 15572227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 2,6-diisopropylaniline (53.1 g, 0.30 mol) and ethyl bromoacetate (55.1 g, 0.33 mol) in 200 ml DMF. After 72 hours, pour onto aqueous NaHCO3 and extract with hexane. Wash the hexane twice with water. Dry, concentrate and distill to obtain as a fraction b.p. 130°-145° C./0.1 mm N-ethoxycarbonylmethyl-(2,6-diisopropyl)aniline.

Workup

  1. extractionextract with hexane
  2. washWash the hexane twice with water
  3. customDry
  4. concentrationconcentrate
  5. distillationdistill

Sources & evidence

ORD record
ord-0826ba71fb6a4287ace3389dadde4140
Source dataset
uspto-grants-1982_03
Patent number
US04322434

Reaction notes

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