Phenyl isocyanate → HCID 54512104, compound

HRID 1463538Notes

Reaction equation

HRID 1463538 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O:34][CH:35]1[CH2:40][C:39]([CH3:42])([CH3:41])[N:38]([OH:43])[C:37]([CH3:45])([CH3:44])[CH2:36]1)(=[O:33])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH:22]1[CH2:27][C:26]([CH3:29])([CH3:28])[N:25]([OH:30])[C:24]([CH3:32])([CH3:31])[CH2:23]1)=[O:20]>ClCCl.CO>[C:10]([O:34][CH:35]1[CH2:36][C:37]([CH3:45])([CH3:44])[N:38]([O:43][C:8](=[O:9])[NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:39]([CH3:42])([CH3:41])[CH2:40]1)(=[O:33])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH:22]1[CH2:23][C:24]([CH3:31])([CH3:32])[N:25]([O:30][C:8](=[O:9])[NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:26]([CH3:28])([CH3:29])[CH2:27]1)=[O:20]

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 11272241Bis(1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl)decandioate

Product 1

HCID 54512104HCID 54512104, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Phenyl isocyanate (9.5 g, 80 mmol) is added over 5 minutes to a suspension of 20.0 g (39 mmol) of di-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate in 125 ml of dichloromethane. The resulting solution is refluxed for 30 minutes and then evaporated to obtain a solid. The crude solid is briefly refluxed in methanol, filtered off, and recrystallized from 2-propanol: dichloromethane to give 22.2g (76% yield) of white solid, m.p. 159-61° C.(dec).

Workup

  1. temperatureThe resulting solution is refluxed for 30 minutes
  2. customevaporated
  3. customto obtain a solid
  4. filtrationfiltered off
  5. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-c806d9018302482f919b577632d6e02b
Source dataset
uspto-grants-1994_04
Patent number
US05300647

Reaction notes

Loading…