Acetyl chloride → HCID 86675139, compound

HRID 587678Notes

Reaction equation

HRID 587678 reaction equation
[Br:1][C:2]1[CH:16]=[C:15](/[CH:17]=[CH:18]/[CH:19]([C:24]2[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=2)[C:20]([F:23])([F:22])[F:21])[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5].[C:33](Cl)(=[O:35])[CH3:34]>C(Cl)Cl>[C:33]([N:10]1[CH2:11][CH2:12][CH:7]([NH:6][C:4](=[O:5])[C:3]2[CH:13]=[CH:14][C:15](/[CH:17]=[CH:18]/[CH:19]([C:24]3[CH:25]=[C:26]([Cl:32])[C:27]([Cl:31])=[C:28]([Cl:30])[CH:29]=3)[C:20]([F:23])([F:21])[F:22])=[CH:16][C:2]=2[Br:1])[CH2:8][CH2:9]1)(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86675137HCID 86675137, compound

Product 1

HCID 86675139HCID 86675139, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (E)-2-bromo-N-(piperidin-4-yl)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamide (0.1 g, 0.16 mmol) in CH2Cl2 (10.0 mL) was added TEA (0.046 mL, 0.35 mmol) and stirred for 10 min. Then acetyl chloride (0.014, 0.18 mmol) was added and stirred for 16 h at ambient temperature. The reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3 solution and brine solution. The combined CH2Cl2 layer was dried over Na2SO4 and concentrated under reduced pressure to afford crude compound. The crude compound was washed with 5% Et2O/n-pentane to afford the title compound as a white solid (0.054 g, 50%).

Workup

  1. stirringstirred for 16 h at ambient temperature
  2. washwashed with saturated NaHCO3 solution and brine solution
  3. dry with materialThe combined CH2Cl2 layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford crude compound
  6. washThe crude compound was washed with 5% Et2O/n-pentane

Sources & evidence

ORD record
ord-f2ef370954d34e898b047675629850c2
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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