4,6-Diethyl-2-methyl-1,3-benzenediamine → HCID 87148504, compound

HRID 500025Notes

Reaction equation

HRID 500025 reaction equation
[CH2:1]([C:3]1[C:8]([NH2:9])=[C:7]([CH3:10])[C:6]([NH2:11])=[C:5]([CH2:12][CH3:13])[CH:4]=1)[CH3:2]>[Pt].C(C(C)=O)C>[CH:1]([NH:11][C:6]1[C:5]([CH2:12][CH3:13])=[CH:4][C:3]([CH2:1][CH3:2])=[C:8]([NH:9][CH:5]([CH2:6][CH3:7])[CH3:12])[C:7]=1[CH3:10])([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 749794,6-Diethyl-2-methyl-1,3-benzenediamine

Product 1

HCID 87148504HCID 87148504, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
120 °C

Procedure

Diethyl(methyl)-1,3-benzenediamine, as a mixture of its 2,4-diethyl-6-methyl- and 4,6-diethyl-2-methyl-isomers (10.0 g; Ethacure® 100, Albemarle Corporation), Pt(S)/C (0.5 g), Amberlyst-15 (0.5 g), and methyl ethyl ketone (50 g) were charged into a 100 mL metal autoclave at 22° C. 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 reaction mixture was then heated at 120° C. under 125 psig (9.63×105 Pa) of H2 for 5.5 hrs (until no further H2 uptake was observed). The product mixture was cooled to 22° C. and degassed. A diluted product sample was analyzed by GC (100° C. for 5 minutes at 10° C. per minute rate; final temperature, 270° C.). The GC data (normalization method) showed 100% conversion of diethyl(methyl)-1,3-benzenediamine, and a 96.5% yield of N,N′-di-sec-butyl-[diethyl(methyl)-1,3-benzenediamine].

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. temperatureThe product mixture was cooled to 22° C.
  4. customdegassed
  5. custom100° C.
  6. customfor 5 minutes
  7. customtemperature, 270° C.

Sources & evidence

ORD record
ord-2962afa639004f0ab8016a30123375ec
Source dataset
uspto-grants-2010_08
Patent number
US07767858B2

Reaction notes

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