N,N-Dimethylaniline → HCID 53939820, compound

HRID 1609576Notes

Reaction equation

HRID 1609576 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.CN(C)C1C=CC=CC=1.ClC([O:27][C:28](Cl)(Cl)Cl)=O.[CH3:32][CH:33]([NH2:40])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38].N1C=CC=CC=1>C1C=CC=CC=1.O1CCOCC1>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]=2[CH:13]=[CH:14][C:2]=1[O:1][C:28](=[O:27])[NH:40][CH:33]([CH3:32])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38]

Participants

8

Reactant 5

HCID 949N,N-DimethylanilineHCID 1049PyridineHCID 10426DiphosgeneHCID 109822-Amino-6-methylheptaneHCID 665872-Dibenzofuranol

Product 1

HCID 53939820HCID 53939820, compoundYield 130.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-hydroxydibenzofuran (5.0 g, 27 mmol) and dimethylaniline (3.4 mL, 27 mmol) in 35 mL of benzene plus 1.5 mL of dioxane was added dropwise under nitrogen to a solution of trichloromethyl chloroformate (1.6 mL, 14 mmol) in 30 mL of benzene at ice bath temperature. After the addition the cooling bath was removed and the stirring continued for approximately 24 hours. The reaction was cooled to ice bath temperature and a solution of 1,5-dimethylhexylamine (4.6 mL, 27 mmol) and pyridine (4.4 mL, 54 mmol) in 30 mL of benzene was added dropwise over 15 minutes. After the addition the reaction was stirred at ice bath temperature for 2 hours. The cooling bath was removed and the stirring continued for approximately 22 hours. The reaction was extracted two times with 1N HCl. The organic solution was dried over anhydrous MgSO4 and the solvent removed under reduced pressure to give 6.19 g of a yellow solid. Recrystallization from isopropanol gave 4.27 g (46%) of the title compound as a yellow crystalline solid, mp 114°-115° C.

Workup

  1. additionAfter the addition the cooling bath
  2. customwas removed
  3. temperatureThe reaction was cooled to ice bath temperature
  4. additionAfter the addition the reaction
  5. customThe cooling bath was removed
  6. waitthe stirring continued for approximately 22 hours
  7. extractionThe reaction was extracted two times with 1N HCl
  8. dry with materialThe organic solution was dried over anhydrous MgSO4
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-606c7fde20c64b2d969872aa39a406a9
Source dataset
uspto-grants-1995_03
Patent number
US05401769

Reaction notes

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