3-(Trifluoromethyl)aniline → HCID 66685205, compound

HRID 1803764Notes

Reaction equation

HRID 1803764 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>ClCCl>[Br:18][CH2:19][CH2:20][C:21]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)=[O:22]

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 11430Potassium CarbonateHCID 84944Propanoyl chloride, 3-bromo-

Product 1

HCID 66685205HCID 66685205, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(Trifluoromethyl)aniline (Aldrich, 16.11 g, 100 mmol) was added to a suspension of potassium carbonate (27.64 g, 200 mmol) in dichloromethane (225 mL) followed by the addition of 3-bromopropionyl chloride (10.08 mL, 100 mmol) in dichloromethane (40 mL). The mixture was stirred for 4 hours at ambient temperature, quenched with water (200 mL), the organic layer was washed twice with water (200 mL), dried over sodium sulfate, filtered through a silica gel plug, and rinsed with 1:1 ethyl acetate:hexane (400 mL), and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.99 (t, J=6.27 Hz, 2H), 3.74 (t, J=6.44 Hz, 2H), 7.41 (d, J=7.80 Hz, 1H), 7.56 (t, J=7.97 Hz, 1H), 7.77 (d, J=8.48 Hz, 1H), 8.11 (s, 1H), 10.39 (s, 1H). MS (DCI) m/z 312.99 (M+NH4)+.

Workup

  1. customquenched with water (200 mL)
  2. washthe organic layer was washed twice with water (200 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered through a silica gel plug
  5. washrinsed with 1:1 ethyl acetate
  6. concentrationhexane (400 mL), and concentrated under reduced pressure

Sources & evidence

ORD record
ord-9a9dc96acd60453fb2177cabe07bb530
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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