Dichloromethane → HCID 178490390, compound

HRID 64540Notes

Reaction equation

HRID 64540 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:5]([NH2:6])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.C[Al](C)C.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25].C(Cl)Cl>C1(C)C=CC=CC=1.CO>[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:10])[CH3:11])[C:5]([NH:6][C:24](=[NH:25])[C:23]2[CH:26]=[CH:27][CH:28]=[C:21]([O:20][CH3:19])[CH:22]=2)=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 737123-MethoxybenzonitrileHCID 117801144-Bromo-2,6-diisopropylanilineHCID 16682925Trimethylaluminum

Product 1

HCID 178490390HCID 178490390, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

One 2 L 3-neck flask was charged with 4-bromo-2,6-diisopropylaniline (19 g, 74.2 mmol) and toluene (200 ml). Trimethylaluminum (2M solution in toluene, 25 ml) was added dropwise into the reaction mixture at 0° C. After the addition was over, the ice bath was removed and reaction mixture was allowed to stir at room temperature (20-25° C.) for 3 hours. 3-methoxybenzonitrile (9.88 g, 74.2 mmol) in toluene (300 ml) was then added into reaction mixture. The reaction mixture was allowed to heated to 80° C. for 17 hours. The reaction mixture was poured slowly into a slurry of 200 gm of celite in 900 ml of a 2:1 mixture of DCM in methanol. The reaction mixture was then filtered and filtrate was evaporated to dryness, the residue was re-suspend with heptane and filtered to yield N-(4-bromo-2,6-diisopropylphenyl)-3-methoxybenzimidamide (19.73 g, 68%).

Workup

  1. additionAfter the addition
  2. customwas removed
  3. customreaction mixture
  4. temperatureto heated to 80° C. for 17 hours
  5. filtrationThe reaction mixture was then filtered
  6. customfiltrate was evaporated to dryness
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a973af09d6a34014ab3bcb036b1f0cc4
Source dataset
uspto-grants-2016_09
Patent number
US09450195B2

Reaction notes

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