Benzene → N,N'-bisacryloyl-2,2-di-(2-aminoethoxy)propane

HRID 1612903Notes

Reaction equation

HRID 1612903 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]([O:8][CH2:9][CH2:10][NH2:11])([CH3:7])[CH3:6].[C:12](Cl)(=[O:15])[CH:13]=[CH2:14].[CH:17]1[CH:22]=CC=C[CH:18]=1.C(=O)([O-])[O-:24].[Na+].[Na+]>CC(C)=O>[C:12]([NH:11][CH2:10][CH2:9][O:8][C:5]([O:4][CH2:3][CH2:2][NH:1][C:18](=[O:24])[CH:17]=[CH2:22])([CH3:6])[CH3:7])(=[O:15])[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 197770192,2-Bis(2-aminoethoxy)propane

Product 1

HCID 15608862N,N'-bisacryloyl-2,2-di-(2-aminoethoxy)propane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2,2-Di-(2-aminoethoxy)propane (11.0 gm, 67.8 mmole) was dissolved in a solution of 450 mL of 0.67 sodium carbonate and 130 mL of acetone and was cooled in an ice bath. Acryloyl chloride (18.1 mL, 223 mmole) dissolved in 150 mL of acetone was added dropwise and the solution stirred overnight. The acetone and water were evaporated in vacuo until the solution was saturated in salts. The solution was then extracted with 6×50 mL of chloroform. The chloroform extracts were combined, dried over sodium sulphate, filtered and the solvent was removed in vacuo to yield a syrup. Crystals were formed on addition of benzene. After evaporation 14.6 gm of crude product was obtained. This material was recrystallised from ethyl acetate and hexane to give 13.1 gm of white crystals: 48.6 mmole, 72%. mp 94°-95° C. NMR δ(CDCl3) 7.0 (br s, 2 H, NH), 5.7-6.5 (m, 4 H, =CH2), 5.50 (tr, 2 H, -CH=), 3.47 (m, 8 H, NCH2CH2O), 1.30 (s, 6 H, geminal (CH3)2). Analysis: C13H22N2O4 requires C, 57.76%; H, 8.20%; N, 10.36%. Found: C, 57.79% H, 8.18%; N, 10.29%.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionwas added dropwise
  3. customThe acetone and water were evaporated in vacuo until the solution
  4. extractionThe solution was then extracted with 6×50 mL of chloroform
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customto yield a syrup
  9. customAfter evaporation 14.6 gm of crude product
  10. customwas obtained
  11. customThis material was recrystallised from ethyl acetate and hexane

Sources & evidence

ORD record
ord-df85572333ef4b5ebb61ddc401b7758e
Source dataset
uspto-grants-1993_03
Patent number
US05191015

Reaction notes

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