Triethylamine → 3-chloro-N-(3-fluorophenyl)propanamide

HRID 1521637Notes

Reaction equation

HRID 1521637 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[Cl:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>ClCCl.O>[Cl:16][CH2:17][CH2:18][C:19]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=1)=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 97423-FluoroanilineHCID 693643-Chloropropionyl chloride

Product 1

HCID 35556953-chloro-N-(3-fluorophenyl)propanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-fluoroaniline (20 g, 0.180 mol) in dichloromethane (100 mL) was added triethylamine (21.816 g, 0.216 mol) and 3-chloropropanoyl chloride (17.18 mL, 0.180 mol) under cooling condition (0° C.) with constant stirring. Reaction mass was allowed to stir at room temperature for 12 h. The reaction mixture was diluted with water (300 mL) and extracted with dichloromethane (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.51-7.48 (d, J=10.4 Hz, 1H), 7.42 (bs, 1H), 7.29-7.24 (dd, J=14.8 Hz, 8.0 Hz, 1H), 7.15-7.13 (d, J=8.0 Hz, 1H), 6.84-6.81 (t, J=6.8 Hz, 1H), 3.89-3.86 (t, J=6.4 Hz, 2H), 2.83-2.80 (t, J=6.4 Hz, 2H). MS (M+1): 201.9.

Workup

  1. customReaction mass
  2. extractionextracted with dichloromethane (4×100 mL)
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b8a90603582e4bbf9ad7dbb5e9516811
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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