Isopropanol → Isopropyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

HRID 1395717Notes

Reaction equation

HRID 1395717 reaction equation
[F:1][C:2]([F:29])([F:28])[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][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.B(F)(F)F.CCOCC.[CH:39](O)([CH3:41])[CH3:40]>>[F:1][C:2]([F:28])([F:29])[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][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O:25][CH:39]([CH3:41])[CH3:40])=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 8000Boron trifluoride etherateHCID 128316104-[15-(Trifluoromethyl)pentadecylamino]benzoic acid

Product 1

HCID 20549354Isopropyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

Procedure

A solution of 50.5 g of 4-[15-(trifluoromethyl)pentadecylamino]benzoic acid and 34.4 ml. of boron trifluoride etherate in 200 ml. of isopropyl alcohol 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 the product 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-e66e36b50ceb4e32b2ddbb46d406d1bc
Source dataset
uspto-grants-1980_05
Patent number
US04205085

Reaction notes

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