Boron trifluoride etherate → Methyl 4-(15-carbomethoxypentadecylamino)benzoate

HRID 904256Notes

Reaction equation

HRID 904256 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)([O:3][CH3:4])=[O:2].B(F)(F)F.[CH3:34]COCC>CO>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:34])=[O:26])=[CH:28][CH:29]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 12898273p-(15-Carbomethoxypentadecylamino)benzoic acid

Product 1

HCID 12898274Methyl 4-(15-carbomethoxypentadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50.5 g. of 4-(15-carbomethoxypentadecylamino)benzoic acid and 34.4 ml. of boron trifluoride etherate in 200 ml. of methanol is stirred under reflux for 4 hours, allowed to cool, and is poured into 1.20 liters of ice cold 5% aqueous sodium carbonate solution. The white solid is collected by filtration and recrystallized from benzene-ethanol to yield methyl 4-(15-carbomethoxypentadecylamino)benzoate, m.p. 92°-93° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureto cool
  3. filtrationThe white solid is collected by filtration
  4. customrecrystallized from benzene-ethanol

Sources & evidence

ORD record
ord-dc61ec9dbb81458986e967d36c11e7b8
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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