Toluene → HCID 54481674, compound

HRID 643189Notes

Reaction equation

HRID 643189 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].C(=O)(O)[O-].[K+].[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:28](#[N:30])[CH3:29]>[Cu]Cl>[C:10]1([CH3:15])[CH:11]=[CH:12][C:13]([N:30]([CH:28]=[CH:29][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:24]2[CH:25]=[CH:26][C:21]([CH3:27])=[CH:22][CH:23]=2)=[CH:14][CH:9]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 51282-IodotolueneHCID 6115AnilineHCID 6342AcetonitrileHCID 516893Potassium Bicarbonate

Product 1

HCID 54481674HCID 54481674, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Conditions

Temperature
160 °C

Procedure

A 2-liter 3-necked round bottom flask equipped with a mechanical stirrer, reflux condenser and thermometer is charged with 139.7 g (1.5 mol) of aniline, 727.2 g (3.3 mol) of iodotoluene, 255.0 g (2.6 mol) of potassium bicarbonate and 0.6 g of copper (I) chloride. The reaction mixture is quickly heated to 160° C. and maintained at 160-180° C. for seven days, after which it is cooled to 110° C. and 350 ml of toluene is added. The insoluble salts therein are filtered off and the filtrate is washed with water several times. The filtrate is concentrated to form an oil under vacuum, after which it is poured into acetonitrile to precipitate the product. The slurry is cooled, and the resulting solid is isolated by filtration and dried under vacuum to give 327.0 g (yield of 80%) of the desired product.

Workup

  1. customA 2-liter 3-necked round bottom flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperaturemaintained at 160-180° C. for seven days
  4. temperatureafter which it is cooled to 110° C.
  5. filtrationThe insoluble salts therein are filtered off
  6. washthe filtrate is washed with water several times
  7. concentrationThe filtrate is concentrated
  8. customto form an oil under vacuum
  9. customto precipitate the product
  10. temperatureThe slurry is cooled
  11. customthe resulting solid is isolated by filtration
  12. customdried under vacuum

Sources & evidence

ORD record
ord-ec38b15fe4e94aaebb48b7452b360fd6
Source dataset
uspto-grants-2010_04
Patent number
US07700248B2

Reaction notes

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