p-Toluenesulfonic acid → HCID 178448982, compound

HRID 254544Notes

Reaction equation

HRID 254544 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:11](/[N:15]=[CH:4]/[C:3]1[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8007ButylamineHCID 678472-Chloro-6-fluorobenzaldehyde

Product 1

HCID 178448982HCID 178448982, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 59.8 g (377 mmol) 2-chloro-6-fluorobenzaldehyde in 250 ml toluene were added 41.0 ml (415 mmol) N-butylamine and 1.44 g (7.54 mmol) p-toluenesulphonic acid. The mixture was heated at reflux for 5 h. After cooling to room temperature, the mixture was diluted with toluene and washed sequentially with aqueous sodium bicarbonate solution, water and saturated brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to afford 80.1 g (99% of the title compound as a dark brown oil which was used in the next step without further purification. MS (ISP): 216.2 ([M+H]+), 214.2 ([M+H]+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 h
  3. washwashed sequentially with aqueous sodium bicarbonate solution, water and saturated brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb5ef2bf9091423a81825240effa6403
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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