Boron trifluoride etherate → HCID 20503602, compound

HRID 850983Notes

Reaction equation

HRID 850983 reaction equation
[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]([OH:25])=[O:24])[S:21][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:26]([O:28][CH2:29][CH2:30]O)[CH3:27].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]([O:25][CH2:27][CH2:26][O:28][CH2:29][CH3:30])=[O:24])[S:21][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 8076Glycol monoethyl etherHCID 131349944-Hexadecylamino-2-thiophenecarboxylic acid

Product 1

HCID 20503602HCID 20503602, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g. of 4-(hexadecylamino)-2-thiophenecarboxylic acid, 1.00 g. of 2-ethoxyethanol and 5.35 ml. of boron trifluoride etherate in 200 ml. of 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-(hexadecylamino)-2-thiophenecarboxylate 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-94dcef544d274b2e8b4a2e3867a88375
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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