Methyl Ethyl Ketone → HCID 68456402, compound

HRID 500037Notes

Reaction equation

HRID 500037 reaction equation
[CH2:1]([C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH2:18])=[C:13]([CH3:19])[CH:12]=1)[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.[CH2:20]([C:22]([CH3:24])=O)[CH3:21]>[Pt].C1(C)C=CC=CC=1>[CH:20]([NH:18][C:14]1[C:15]([CH3:17])=[CH:16][C:11]([CH2:1][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][CH:1]([CH2:2][CH3:3])[CH3:11])=[C:4]([CH3:10])[CH:3]=2)=[CH:12][C:13]=1[CH3:19])([CH2:22][CH3:24])[CH3:21]

Participants

5

Reactant 2

HCID 6569Methyl Ethyl KetoneHCID 776904,4'-Methylenebis(2,6-xylidine)

Product 1

HCID 68456402HCID 68456402, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
22 °C

Procedure

4,4′-Methylenebis(2,6-dimethylbenzeneamine) (1.25 g), methyl ethyl ketone (15 g), Pt(S)/C (0.10 g), and toluene (40.0 g) were charged into reactor. The reactor was purged 3 times with 110 psig (8.60×105 Pa) of H2 at 22° C. The reaction mixture was then stirred at 22° C. under 110 psig (8.60×105 Pa) of H2 for 4.5 hours. GC (conditions:100° C./5 minutes/10° C.-minute/270° C.) showed 35% conversion of 4,4′-methylenebis(2,6-dimethylbenzeneamine). The reaction mixture was then stirred for 4 hours at 60° C., after which GC showed 79.5% conversion of 4,4′-methylenebis(2,6-dimethylbenzeneamine). The reaction mixture was then stirred for 11 hours at 130° C., after which GC showed 100% conversion of4,4′-methylenebis(2,6-dimethylbenzeneamine), and a 96% yield of N,N′-di-sec-butyl-4,4′-methylenebis(2,6-dimethylbenzeneamine); the remaining 4% was determined to be N-sec-butyl-4,4′-methylenebis(2,6-dimethylbenzeneamine). The product was observed to be water-white in color, and the structure of the product was confirmed by GC-MS.

Workup

  1. customThe reactor was purged 3 times with 110 psig (8.60×105 Pa) of H2 at 22° C
  2. customGC (conditions:100° C./5 minutes/10° C.-minute/270° C.)
  3. stirringThe reaction mixture was then stirred for 4 hours at 60° C.
  4. stirringThe reaction mixture was then stirred for 11 hours at 130° C.

Sources & evidence

ORD record
ord-620a087f2dac475698a2dc7fc0b06e5f
Source dataset
uspto-grants-2010_08
Patent number
US07767858B2

Reaction notes

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