1,2-Dibromoethane → 6-(2-Bromoethoxy)salicylamide

HRID 1462360Notes

Reaction equation

HRID 1462360 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][CH2:20]Br>C(#N)C>[Br:18][CH2:19][CH2:20][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 766022,6-Dihydroxybenzamide

Product 1

HCID 137544236-(2-Bromoethoxy)salicylamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 23.0 g of 2,6-dihydroxybenzamide, 20.7 g of potassium carbonate and 28.2 g of 1,2-dibromoethane in 300 ml of acetonitrile is stirred under reflux for 2-3 hours. The reaction mixture is filtered whilst still warm, the filtrate is evaporated and the residue is recrystallised from a little methanol. 6-(2-Bromoethoxy)salicylamide with a melting point of 120°-121° is obtained.

Workup

  1. temperatureunder reflux for 2-3 hours
  2. filtrationThe reaction mixture is filtered
  3. temperaturewhilst still warm
  4. customthe filtrate is evaporated
  5. customthe residue is recrystallised from a little methanol

Sources & evidence

ORD record
ord-49770e2ac2594147b3c911489fde6c82
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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