Formic Acid → HCID 17969131, compound

HRID 1296732Notes

Reaction equation

HRID 1296732 reaction equation
[CH3:1][C:2](=O)[C:3](=O)[CH2:4][CH2:5][CH3:6].[CH3:9][C:10]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:11]=1[NH2:12].C(O)=O>CO>[CH3:1][C:2]([C:3]([CH2:4][CH2:5][CH3:6])=[N:12][C:11]1[C:13]([CH3:17])=[CH:14][CH:15]=[CH:16][C:10]=1[CH3:9])=[N:12][C:11]1[C:13]([CH3:17])=[CH:14][CH:15]=[CH:16][C:10]=1[CH3:9]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 68962,6-DimethylanilineHCID 197072,3-Hexanedione

Product 1

HCID 17969131HCID 17969131, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,3-Hexanedione (4.0 mL, 33 mmol) was slowly added to the mixture of 2,6-dimethylaniline (10 g, 80 mmol) and 0.2 mL formic acid in 25 mL of methanol. The mixture was stirred for 6 hours. After this time period, the solvent and excess of aniline were removed under vacuum. The residual viscous oil was dissolved in n-pentane and cooled to give a yellow solid which was recrystallized from n-pentane. The product, 2-methyl-3-propyl-1,4-bis(2,6-dimethylphenyl)-1,4-diaza-1,3-butadiene was isolated as yellow crystals (1.9 g, 18%). 1H NMR (200 MHz, CDCl3, δ, ppm): 0.84 t (3H, J=7.28 Hz, (CH2)2CH3); 1.52 m (2H, CH2CH2CH3); 2.03 s (3H, N═CCH3); 2.05 s and 2.06 s (6H and 6H, 2,6- and 2′,6′-CH3); 2.50 m (2H, CH2CH2CH3); 6.89-7.15 m (6H, 2×C6H3). 13C NMR (50.3 MHz, CDCl3, δ, ppm): 14.59 (CH2CH2CH3); 16.38 (N═CCH3); 17.96 and 18.03 (0.2,6- and 2′, 6′-CCH3); 20.28 (CH2CH2CH3); 31.24 (CH2CH2CH3); 123.13 and 123.18 (4- and 4′-CH); 124.67 and 124.75 (2,6 and 2′,6′-C); 127.94 and 127.98 (3,5- and 3′,5′-CH); 147.99 (140 -C); 148.51 (1-C); 167.61 (N═CMe); 171.52 (N═CPr).

Workup

  1. customAfter this time period, the solvent and excess of aniline were removed under vacuum
  2. dissolutionThe residual viscous oil was dissolved in n-pentane
  3. temperaturecooled
  4. customto give a yellow solid which
  5. customwas recrystallized from n-pentane

Sources & evidence

ORD record
ord-e33f15d147844f06889da4acccf8b1cd
Source dataset
uspto-grants-2007_07
Patent number
US07247687B2

Reaction notes

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