Boron trifluoride etherate → 2-Ethoxyethyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

HRID 2057663Notes

Reaction equation

HRID 2057663 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.[CH2:31]([O:33][CH2:34][CH2:35]O)[CH3:32].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[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][CH2:32][CH2:31][O:33][CH2:34][CH3:35])=[O:27])=[CH:29][CH:30]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 8076Glycol monoethyl etherHCID 203309694-[13-(4-Chlorophenyl)-12-tridecynylamino]benzoic acid

Product 1

HCID 203312852-Ethoxyethyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g. of 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoic acid, 1.00 g. of 2-ethoxyethanol and 5.35 ml. of boron trifluoride etherate in 200 ml. toluene is stirred under reflux for 48 hours. The solution is treated with an additional 5.35 ml. of boron trifluoride etherate and refluxing is continued for 120 hours. Dilution with water and methylene chloride followed by filtration affords 2-ethoxyethyl 4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoate as a white solid.

Workup

  1. temperatureunder reflux for 48 hours
  2. additionThe solution is treated with an additional 5.35 ml
  3. filtrationDilution with water and methylene chloride followed by filtration

Sources & evidence

ORD record
ord-3c3371b78909449b82ba8701db3f9855
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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