Toluene → HCID 11228253, compound

HRID 2181344Notes

Reaction equation

HRID 2181344 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])C.[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:19](=[N:16][C:17]1[C:18]([CH:9]([CH3:10])[CH3:8])=[CH:23][CH:24]=[CH:25][C:26]=1[CH:21]([CH3:22])[CH3:27])[C:20]1[CH:7]=[CH:5][CH:4]=[CH:1][CH:2]=1)([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 1140TolueneHCID 8471TriethylamineHCID 32484Diisopropylaniline2×

Product 1

HCID 11228253HCID 11228253, compoundYield 85%

Procedure

Alternatively, the compound was prepared from the corresponding imidoyl chloride and 2,6-diisopropyl aniline. A solution of 2,6-diisopropylaniline (0.885 g, 5 mmol), triethylamine (2.5 mL), and N-2,6-diisopropylbenzimidoyl chloride (1.50 g, 5 mmol) in 10 mL of toluene was refluxed for 24 h. The mixture was washed with water, dried (over Na2SO4), and concentrated. After a single crystallization from ethanol/water, 1.88 g (85%) of the benzamidine was obtained; it was identical to the compound described above as seen by MP and NMR spectroscopy.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried (over Na2SO4)
  3. concentrationconcentrated
  4. customAfter a single crystallization from ethanol/water

Sources & evidence

ORD record
ord-a0a5ac75a6a44a8dbc7f6686679715e0
Source dataset
uspto-grants-2005_05
Patent number
US06891006B2

Reaction notes

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