Dichloromethane → HCID 178492405, compound

HRID 539457Notes

Reaction equation

HRID 539457 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[Al](C)C.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:32]#[N:33])[CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=1.C(Cl)Cl>C1(C)C=CC=CC=1.CO>[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:32]([C:22]1[CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=[C:20]([O:19][CH3:18])[CH:21]=1)=[NH:33])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 32484DiisopropylanilineHCID 16682925TrimethylaluminumHCID 706544735-Methoxy-[1,1'-biphenyl]-3-carbonitrile

Product 1

HCID 178492405HCID 178492405, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

To a 500 mL 3 neck flask, 2,6-diisopropylaniline (4.99 g, 27.3 mmol) and 100 mL toluene were charged. The mixture was cooled down in ice bath. Trimethylaluminum (20.48 mL, 41.0 mmol) was added dropwise via additional funnel. The reaction mixture was stirring at RT for 2 hours. Then, to the mix, added 5-methoxy-[1,1′-biphenyl]-3-carbonitrile (6.0 g, 28.7 mmol) dissolved in 50 mL toluene. The reaction mixture was heated to 70° C. overnight under a nitrogen atmosphere. The reaction mixture was cooled in an ice bath and poured it into silica gel mixed with DCM and methanol (2:1 ratio of DCM:methanol). The slurry was stirred and filtered and washed with DCM and methanol. The solvent was evaporated. The solid remaining after evaporation of solvent was added to 150 mL hexane and the mixture was stirred. The mixture was filtered and washed with hexane. After removal of solvent, 6.8 g of product was obtained for next step.

Workup

  1. temperatureThe mixture was cooled down in ice bath
  2. temperatureThe reaction mixture was heated to 70° C. overnight under a nitrogen atmosphere
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. additionpoured it into silica gel
  5. stirringThe slurry was stirred
  6. filtrationfiltered
  7. washwashed with DCM and methanol
  8. customThe solvent was evaporated
  9. customafter evaporation of solvent
  10. additionwas added to 150 mL hexane
  11. stirringthe mixture was stirred
  12. filtrationThe mixture was filtered
  13. washwashed with hexane
  14. customAfter removal of solvent

Sources & evidence

ORD record
ord-2e0ae901ec6a482b9d222c374d8945aa
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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