N,N'-Diphenyl-P-Phenylenediamine → HCID 66643588, compound

HRID 1026367Notes

Reaction equation

HRID 1026367 reaction equation
[C:1]1([C:7]([S:10][CH2:11][CH2:12][OH:13])([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(NC2C=CC(NC3C=CC=CC=3)=CC=2)C=CC=CC=1.[C:34](OCC)(=[O:37])[CH:35]=[CH2:36]>>[C:34]([O:13][CH2:12][CH2:11][S:10][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:9])[CH3:8])(=[O:37])[CH:35]=[CH2:36]

Participants

4

Reactant 3

HCID 6319N,N'-Diphenyl-P-PhenylenediamineHCID 8821Ethyl AcrylateHCID 66643495HCID 66643495, compound

Product 1

HCID 66643588HCID 66643588, compound

Conditions

Temperature
120 °C

Procedure

Into a 3-neck 250 mL round-bottomed flask were weighed, in the following order: 2-(2-phenylpropan-2-ylthio)ethanol (30.0 g, 0.1528 moles), N,N′-diphenyl-1,4-phenylene diamine (0.318 g, 1.2224×10−3 moles) and ethyl acrylate (122.40 g, 1.2224 moles). The apparatus was then assembled in a reactive distillation arrangement before being purged with N2 (g). The Claisen head of the distillation apparatus was wrapped with Al-foil/glass wool. The reaction flask was then heated to 120° C., by use of a silicone heating oil bath, and once the ethyl acrylate (Bpt: 99° C.) started to distil over tetrapropoxytitanate (TPT) (1.04 mL, 0.999 g, 3.5144×10−3 moles) was added to the reaction mixture via a 2.50 mL Hamilton gastight syringe. The distillation rate immediately increased significantly and the distillation vapour temperature decreased from 98° C. to ca. 80° C.

Workup

  1. customInto a 3-neck 250 mL round-bottomed flask were weighed, in the following order
  2. distillationThe apparatus was then assembled in a reactive distillation arrangement
  3. custombefore being purged with N2 (g)
  4. customthe ethyl acrylate (Bpt: 99° C.)
  5. customto distil over tetrapropoxytitanate (TPT) (1.04 mL, 0.999 g, 3.5144×10−3 moles)
  6. additionwas added to the reaction mixture via a 2.50 mL Hamilton gastight syringe
  7. temperatureThe distillation rate immediately increased significantly
  8. distillationthe distillation
  9. customdecreased from 98° C. to ca. 80° C.

Sources & evidence

ORD record
ord-6b46c2a4e11742d2b29d1684938c7522
Source dataset
uspto-grants-2014_05
Patent number
US08729203B2

Reaction notes

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