2,4,6-Trimethylaniline → HCID 10537962, compound

HRID 1884337Notes

Reaction equation

HRID 1884337 reaction equation
Br[CH2:2][C:3](=[C:5]([C:8]#[N:9])[C:6]#[N:7])[CH3:4].[CH3:10][C:11]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:12]=1[NH2:13]>C(O)(C)C>[NH2:7][C:6]1[N:13]([C:12]2[C:14]([CH3:19])=[CH:15][C:16]([CH3:18])=[CH:17][C:11]=2[CH3:10])[CH:2]=[C:3]([CH3:4])[C:5]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 10921206HCID 10921206, compound

Product 1

HCID 10537962HCID 10537962, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture 2-(2-bromo-1-methyl-ethyl idene)-malononitrile and 2,4,6-trimethylaniline (17.330 g, 91.24 mmol) in 40 mL of isopropanol was stirred at room temperature for 15 hours. The reaction mixture was concentrated to dryness and diluted with chloroform and water. The chloroform layer was neutralized with dilute sodium hydroxide and washed with brine, separated, dried and concentrated to give 33.000 g of brown oily solid. The solid was purified through silica gel column chromatography to give 9.35 g (47.5%) of the title compound as an orange-yellow solid. 1H NMR (CDCl3) δ 2.0(s, 6H), 2.15(s, 3H), 2.35(s, 3H), 3.75(brs, 2H), 5.8(s, 1H), 6.95(s, 2H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted with chloroform and water
  3. washwashed with brine
  4. customseparated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5bfd974caf0b4150b545c7360deea656
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Reaction notes

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