Isobutyraldehyde → HCID 20231523, compound

HRID 482635Notes

Reaction equation

HRID 482635 reaction equation
C(=O)C(C)C.O.NN.C=CC=C.[CH:13]([CH:16]1[CH2:27][CH:26]=[CH:25][CH2:24][CH2:23][CH:22]=[CH:21][CH2:20][CH:19]([CH:28]([CH3:30])[CH3:29])[N:18]=[N:17]1)([CH3:15])[CH3:14].[H][H]>C(O)(C)(C)C.[Rh].[Ni]>[NH2:17][CH:16]([CH:13]([CH3:15])[CH3:14])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]([NH2:18])[CH:28]([CH3:29])[CH3:30]

Participants

9

Reactant 5

HCID 6561IsobutyraldehydeHCID 78451,3-ButadieneHCID 24654Hydrazine hydrate (1:1)HCID 56635899HCID 56635899, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20231523HCID 20231523, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23948RhodiumCatalystHCID 6386tert-ButanolSolvent

Procedure

Isobutgraldazine is prepared by causing isobutyraldehyde to react with hydrazine hydrate according to the operating conditions described in Example 1. One then carries out the cyclooligomerization reaction of the azine with the butadiene by using a molar ratio of 1/3 and by operating as in Example 1 (1 at. g of Ni for 20 moles of azine). In 100 ml of tert. butanol, 14 g of 3,12-diisopropyl-1,2-diaza-1,5,9 cyclododecatriene are hydrogenated in a 300-ml autoclave, in the presence of 1.4 g of rhodium catalyst deposited at 5% on alumina. The reaction is allowed to take place for 30 minutes under 100 bars of hydrogen at 30° C., then one maintains a temperature level of 160° C. under 200 bars of hydrogen for 25 hours. 12 g of the 1,10-diamino-1,10-diisopropyl decane thus obtained are chlorhydrated and phosgenated in the same manner as in Example 1. One recovers 13.2 g of 1,10 -diisopropyl-1,10-diisocyanate (phosgenation yield: 92% with respect to the amine) having an NCO group content of 1.85 equivalents per mole and presenting the following N.M.R. characteristics of the 13C atom (chemical shifts expressed in relation to CDCl3 at 77 ppm): ##STR11##

Workup

  1. customIsobutgraldazine is prepared
  2. customfor 30 minutes
  3. customat 30° C.
  4. customa temperature level of 160° C.
  5. customfor 25 hours

Sources & evidence

ORD record
ord-c13efd2f2bde4b29bf9c3ee3d6b3de74
Source dataset
uspto-grants-1986_03
Patent number
US04574059

Reaction notes

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