Propanal → HCID 15524246, compound

HRID 2296919Notes

Reaction equation

HRID 2296919 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:19](=O)[CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:19](=[N:7][C:6]1[CH:8]=[CH:9][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][CH:5]=1)[CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 527PropanalHCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 11430Potassium Carbonate

Product 1

HCID 15524246HCID 15524246, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4-trifluoromethylaniline (3.3 g, 20.5 mmol) and triethyl amine (8.3 g, 83 mmol) in 100 mL of dichloromethane, cooled in an ice/water bath, was added slowly titanium tetrachloride (11.4 mL of a 1.0M solution in dichloromethane, 11.4 mmol). After 25 min, propionaldehyde (1.8 g, 25.6 mmol) was added slowly as a solution in dichloromethane. After an additional hour of stirring in the ice/water bath, an aqueous potassium carbonate solution was added (˜100 mL of a 1M solution). The organic phase was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the crude title product which was used without further purification. 1H NMR (CDCl3) δ 1.2 (t, 3H), 2.5 (dq, 2H), 7.05 (d, 2H), 7.56 (d, 2H), 7.84 (t, 1H, J=4.4 Hz).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f16659413d074d31885d56780239c7a5
Source dataset
uspto-grants-2002_12
Patent number
US06489478B1

Reaction notes

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