Salicylamide → HCID 12254268, compound

HRID 1288298Notes

Reaction equation

HRID 1288298 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[Na]>C(O)C>[CH2:11]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH2:10])=[O:9])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 81731-BromodecaneHCID 5360545Sodium

Product 1

HCID 12254268HCID 12254268, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Salicylamide (27.4 g.) and decyl bromide (48.3 ml.) were added to a solution of sodium (4.6 g.) in ethanol (175 ml.) and the mixture was heated to reflux with stirring for 2.25 hours. Most of the ethanol was removed by evaporation in vacuo and the residue was poured into water (350 ml.). The oil which separated solidified, and was filtered off and triturated with 2N sodium hydroxide (150 ml.). The solid was filtered off, washed with water (100 ml.), dried over phosphoric oxide, and recrystallised from light petroleum (b.p. 40°-60° C.) to give 2-decyloxybenzamide (40.5 g.), m.p. 58°-59° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customMost of the ethanol was removed by evaporation in vacuo
  4. additionthe residue was poured into water (350 ml.)
  5. customThe oil which separated
  6. filtrationwas filtered off
  7. customtriturated with 2N sodium hydroxide (150 ml.)
  8. filtrationThe solid was filtered off
  9. washwashed with water (100 ml.)
  10. dry with materialdried over phosphoric oxide
  11. customrecrystallised from light petroleum (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-372b95fe538442939e914d166aca0063
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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