Boron trifluoride etherate → Methyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

HRID 2057664Notes

Reaction equation

HRID 2057664 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.B(F)(F)F.[CH3:35]COCC>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:35])=[O:27])=[CH:29][CH:30]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 203309694-[13-(4-Chlorophenyl)-12-tridecynylamino]benzoic acid

Product 1

HCID 20330962Methyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50.5 g. of 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoic acid and 34.4 ml. of boron trifluoride etherate in 200 ml. of methanol is stirred under reflux for 44 hours, allowed to cool, and 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-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate.

Workup

  1. temperatureunder reflux for 44 hours
  2. temperatureto cool
  3. filtrationThe white solid is collected by filtration
  4. customrecrystallized from benzene-ethanol

Sources & evidence

ORD record
ord-7a02d937274a4a2e90a283418358bd0a
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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