Ethanol → Ethyl 2-((3-bromophenyl)amino)acetate

HRID 2229841Notes

Reaction equation

HRID 2229841 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:19](O)[CH3:20]>>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]([O:12][CH2:19][CH3:20])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 17605790HCID 17605790, compound

Product 1

HCID 302657Ethyl 2-((3-bromophenyl)amino)acetate

Conditions

Temperature
80 °C

Procedure

A mixture of 21.3 g of 3-bromophenylglycine in 160 cm3 of 6.5N hydrochloric ethanol is heated with stirring for 24 hours at a temperature in the region of 80° C. The reaction medium is filtered and the filter cake is then washed with twice 30 cm3 of ethanol. The filtrate is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. An oil is obtained, which is basified by addition of aqueous sodium carbonate solution. The mixture is extracted with 3 times 100 cm3 of ethyl acetate. The extracts are combined, washed with twice 100 cm3 of aqueous sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 4.7 g of ethyl 3-bromophenylglycinate are obtained in the form of a yellow oil. (Rf=0.38 in a 90/5 by volume dichloromethane/methanol mixture, on a Merck 60F254R silica plate).

Workup

  1. temperatureis heated
  2. filtrationThe reaction medium is filtered
  3. washthe filter cake is then washed with twice 30 cm3 of ethanol
  4. concentrationThe filtrate is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  5. customAn oil is obtained
  6. extractionThe mixture is extracted with 3 times 100 cm3 of ethyl acetate
  7. washwashed with twice 100 cm3 of aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-6f6555e946f1412584db1f555879dd64
Source dataset
uspto-grants-2002_07
Patent number
US06420566B2

Reaction notes

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