Boron trifluoride etherate → Methyl 4-(hexadecylamino)-2-thiophenecarboxylate

HRID 850981Notes

Reaction equation

HRID 850981 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].B(F)(F)F.[CH3:30]COCC>CO>[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]([O:25][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

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 131349944-Hexadecylamino-2-thiophenecarboxylic acid

Product 1

HCID 20503593Methyl 4-(hexadecylamino)-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50.5 g. of 4-(hexadecylamino)-2-thiophenecarboxylic 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-(hexadecylamino)-2-thiophenecarboxylate as a white solid.

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-aec7829590324d70a799d7fa9f248d7a
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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