Ethanol → HCID 59827189, compound

HRID 1182416Notes

Reaction equation

HRID 1182416 reaction equation
[C:1](=[N:4][C:5]1[C:10]([CH2:11][CH3:12])=[CH:9][C:8]([CH2:13][C:14]2[CH:19]=[C:18]([CH2:20][CH3:21])[C:17]([N:22]=[C:23]([CH3:25])[CH3:24])=[C:16]([CH2:26][CH3:27])[CH:15]=2)=[CH:7][C:6]=1[CH2:28][CH3:29])([CH3:3])[CH3:2].C(O)C>[Pt].C(OCC)(=O)C>[CH:23]([NH:22][C:17]1[C:16]([CH2:26][CH3:27])=[CH:15][C:14]([CH2:13][C:8]2[CH:7]=[C:6]([CH2:28][CH3:29])[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[C:10]([CH2:11][CH3:12])[CH:9]=2)=[CH:19][C:18]=1[CH2:20][CH3:21])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 702EthanolHCID 86608149HCID 86608149, compound

Product 1

HCID 59827189HCID 59827189, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N,N′-diisopropylidene-4,4′-methylenebis(2,6-diethylbenzeneamine) (2.6 g) and Pt(S)/C (0.35 g) were added to a mixture of ethanol (20 g) and ethyl acetate (20 g) in an autoclave. The closed autoclave was purged 3 times with 125 psig (9.63×105 Pa) of H2 at 22° C. to remove traces of air. The mixture was kept at 22° C. and 0-125 psi (0 to 8.62×105 Pa) of H2 for 1.2 hours, forming the corresponding N,N′-diisopropyl-4,4′-methylenebis(2,6-diethylbenzeneamine) in 70% yield, with 25% of the diimine underhydrogenated. Conversion of the diimine was 95%.

Workup

  1. customThe closed autoclave was purged 3 times with 125 psig (9.63×105 Pa) of H2 at 22° C.
  2. customto remove traces of air
  3. customwas kept at 22° C.

Sources & evidence

ORD record
ord-094057febfe0445b84279f0568b01ae9
Source dataset
uspto-grants-2007_10
Patent number
US07288677B2

Reaction notes

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