1,4-Dioxane → HCID 88852449, compound

HRID 1472992Notes

Reaction equation

HRID 1472992 reaction equation
[CH2:1]([O:19][C:20](=[O:31])[CH:21]([NH2:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)[CH2:2][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][CH3:18].Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl.[O:44]1CCOC[CH2:45]1>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([O:19][C:20](=[O:31])[CH:21]([N:30]=[C:45]=[O:44])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:33]=[O:35])=[CH:25][CH:24]=1)[CH2:2][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][CH3:18]

Participants

5

Reactant 3

HCID 312751,4-Dioxane2×HCID 94429TriphosgeneHCID 68161053HCID 68161053, compound

Product 1

HCID 88852449HCID 88852449, compound

Reagents, catalysts & solvents 1

HCID 21889329Toluene hexaneSolvent

Conditions

Temperature
80 °C

Procedure

Into a solution of 2-Amino-3-(4-amino-phenyl)-propionic acid octadecyl ester (100 g) in dry 1,4-dioxane (2000 ml) under Nitrogen atmosphere maintained at 20° C. was added a solution of triphosgene (163 g) in 1,4-Dioxane (200 ml) in one lot. The reaction mixture was heated and refluxed for 3 hours. The condenser was then arranged for distillation and solvent removed by distillation at atmospheric pressure until the volume of the reaction mixture was reduced to approximately one third. Fresh dry dioxane (200 ml) was added and distilled off under vacuum. The residue was dissolved in Toluene (200 ml) and charcoal (5 g) was added. The solution was filtered hot and the solvent was distilled under vacuum to yield crude diisocyanate which was again dissolved in a mixture of toluene: hexane (6:4; 400 ml) by heating to 80° C. for 15 minutes. The solution was filtered and the solvent mixture was distilled off under vacuum. Hexane was added to the precipitate and pure diisocyanate was filtered, dried and packed in tight container to yield 65 g of pure 2-Isocyanato-3-(4-Isocyanato-phenyl)-propionic acid octadecyl ester as a white powder with a melting point of 78-80° C. The product was further characterized by IR: 2261 cm-1 and IH NMR (CDCl3) δ 3.15-3.30 (m, 2H, CH2), 3.70 (s, 3H, OCH3), 5.05 (m, 1H, CH), 6.60 (d, 1H, NH), 7.00 (d, 2H, Ar), 7.05 (d, 2H, Ar), 7.15 (d, 2H, Ar), 7.60 (d, 2H, Ar)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxed for 3 hours
  3. distillationThe condenser was then arranged for distillation and solvent
  4. customremoved by distillation at atmospheric pressure until the volume of the reaction mixture
  5. additionFresh dry dioxane (200 ml) was added
  6. distillationdistilled off under vacuum
  7. dissolutionThe residue was dissolved in Toluene (200 ml)
  8. additioncharcoal (5 g) was added
  9. filtrationThe solution was filtered hot
  10. distillationthe solvent was distilled under vacuum
  11. customto yield crude diisocyanate which
  12. filtrationThe solution was filtered
  13. distillationthe solvent mixture was distilled off under vacuum
  14. additionHexane was added to the precipitate and pure diisocyanate
  15. filtrationwas filtered
  16. customdried

Sources & evidence

ORD record
ord-861537ad0e7f4be5862a25f301e7c062
Source dataset
uspto-grants-2015_04
Patent number
US09012677B2

Reaction notes

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