p-Toluenesulfonic acid → 3-Hydroxypropyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

HRID 1395715Notes

Reaction equation

HRID 1395715 reaction equation
[F:1][C:2]([F:30])([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:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1.C(O)[CH2:32][CH2:33][OH:34].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:1][C:2]([F:29])([F:30])[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:28]=[CH:27][C:22]([C:23]([O:25][CH2:26][CH2:32][CH2:33][OH:34])=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 20549341Methyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

Product 1

HCID 205493503-Hydroxypropyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

Procedure

A mixture of 2.25 g. of methyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate, 280 mg. of 1,3-propanediol and 1.37 g. of p-toluenesulfonic acid is heated at 180° C. for 18 hours and then is partitioned between ether and 3% aqueous sodium carbonate solution. The ether layer is separated, dried, and evaporated to yield the product as a white solid.

Workup

  1. additionA mixture of 2.25 g
  2. customis partitioned between ether and 3% aqueous sodium carbonate solution
  3. customThe ether layer is separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-8f0bc251833743079f3d320deaf9a440
Source dataset
uspto-grants-1980_05
Patent number
US04205085

Reaction notes

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