Diethylamine → HCID 5258522, compound

HRID 2100561Notes

Reaction equation

HRID 2100561 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21]>C(Cl)Cl.CN(C=O)C>[CH2:20]([N:22]([CH2:23][CH3:24])[C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[C:2]([F:1])([F:13])[F:12])[CH3:21]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 98992-(Trifluoromethyl)benzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 5258522HCID 5258522, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-trifluoromethylbenzoic acid (20.0 g, 105 mmol) in 500 mL of methylene chloride was added oxalyl chloride (18.4 mL, 210 mmol) followed by ˜8 drops of DMF. The reaction was allowed to stir at ambient temperature for 4 h and then was concentrated in vacuo to a solid. The solid was taken up in 500 mL of methylene chloride and then there was added diethylamine (24 mL, 231 mmol) dropwise as a solution in 50 mL of methylene chloride. The resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was concentrated in vacuo. The residue was diluted with EtOAc, washed sequentially with 1N HCl, sat'd. aq. NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated to afford 22 g (85%) of the title compound as an oil. 1H NMR (CDCl3): δ 7.68 (d, 1H, J=7.7 Hz), 7.57 (t, 1H, J=7.4 Hz), 7.49 (t, 1H, J=7.7 Hz), 7.32 (d, 1H, J=7.1 Hz), 3.90-3.82 (m, 2H), 3.29-3.22 (m, 2H), 1.23 (t, 3H, J=7.2 Hz), 1.03 (t, 3H, J=7.2 Hz). LRMS (ESI): 246.12 (M+H)+.

Workup

  1. concentrationwas concentrated in vacuo to a solid
  2. stirringto stir at ambient temperature for 18 h
  3. concentrationThe reaction was concentrated in vacuo
  4. additionThe residue was diluted with EtOAc
  5. washwashed sequentially with 1N HCl
  6. dry with materialaq. NaHCO3 and brine, dried (MgSO4)
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-662b1ca20d3a40d9a9dbd6940a7153df
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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