Butanedione → HCID 589661, compound

HRID 1164442Notes

Reaction equation

HRID 1164442 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[CH3:10][C:11](=O)[C:12](=O)[CH3:13]>C(O)C>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[N:4]=[C:11]([C:12](=[N:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])[CH3:13])[CH3:10]

Participants

4

Reactant 2

HCID 650ButanedioneHCID 68962,6-Dimethylaniline

Product 1

HCID 589661HCID 589661, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 37.2 ml (36.3 g, 0.3 moles) of 2,6-dimethylaniline, 13.1 ml (12.9 g, 0.15 moles) of 2,3-butanedione and 100 ml of ethanol is boiled for 12 hours. The solvent is evaporated under reduced pressure, 80 ml of water and 20 ml of acetic acid are added to the residue, and the resulting mixture is stirred for 6 hours at 0° to ±5° C. The mixture is allowed to stand overnight, thereafter the separated precipitate is filtered off, washed with water and dried. 34.0 g (77.5%) of crude 2,3-bis(2',6'-dimethylphenyl-imino)-butane are obtained; m.p.: 78°-86° C. After recrystallization from ethanol 25.1 g (57.2%) of the pure substance, melting at 88°-90° C., are obtained.

Workup

  1. customThe solvent is evaporated under reduced pressure, 80 ml of water and 20 ml of acetic acid
  2. additionare added to the residue
  3. customto ±5° C
  4. waitto stand overnight
  5. filtrationthe separated precipitate is filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-59b233e5ed0d4a5fa27fffc6038de4af
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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