p-Toluenesulfonic acid → HCID 68770745, compound

HRID 1174440Notes

Reaction equation

HRID 1174440 reaction equation
[CH2:1]([C:8]1([CH:17]=[CH:16][C:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:14][CH2:13]1)[CH2:9][CH:10]([OH:12])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](O)(=[O:28])[CH:26]=[CH2:27].CC1C=CC(S(O)(=O)=O)=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>C1(C)C=CC=CC=1>[C:25]([O:12][CH:10]([NH2:11])[CH2:9][C:8]1([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:13]=[CH:14][C:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH2:17]1)(=[O:28])[CH:26]=[CH2:27]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 68771177HCID 68771177, compound

Product 1

HCID 68770745HCID 68770745, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

In a three-aperture flask, 10.5 g (33 mmol) of p-dibenzyl-aminophenethyl alcohol, 9.51 g (132 mmol) of acrylic acid, 0.56 g (3.3 mmol) of p-toluene sulfonate, and 30 mL of dehydrated toluene were poured, and the mixture was heated at 80° C. under an argon atmosphere with stirring. To the reaction solution, 3.8 g (18.2 mmol) of dicyclohexylcarbodimide and 2.5 g (16.5 mmol) of 4-pyrrolidinopyridine were added, and the reaction solution was further heated with stirring for 5 hours. The reaction solution was cooled to the room temperature and then diluted with toluene, followed by washing with water three times. The toluene solution was dried with anhydrous magnesium sulfate, and then the solvent was distilled away to purify the toluene solution by silica gel chromatography using a mixture solvent of hexane/ethyl acetate (4/1) as an eluent to thereby synthesize 4.05 g (yield: 33% by mass) of p-dibenzyl-aminophenethyl acrylate of the exemplified compound No. 23 represented by the following structural formula.

Workup

  1. temperaturethe reaction solution was further heated
  2. stirringwith stirring for 5 hours
  3. temperatureThe reaction solution was cooled to the room temperature
  4. washby washing with water three times
  5. dry with materialThe toluene solution was dried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away
  7. customto purify the toluene solution by silica gel chromatography
  8. customto thereby synthesize 4.05 g (yield: 33% by mass) of p-dibenzyl-aminophenethyl acrylate of the exemplified compound No

Sources & evidence

ORD record
ord-53b8a2c5c5834be8b07ea5e67d32e087
Source dataset
uspto-grants-2010_11
Patent number
US07838188B2

Reaction notes

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